research communications
Synthesis and II coordination polymer: poly[(μ3-3-carboxybenzoato)[μ2-5-(pyridin-4-yl)-1H,2′H-3,3′-bi[1,2,4-triazole]]cobalt(II)]
of a two-dimensional CoaDepartment of Biology and Chemical Engineering, Nanyang Institute of Technology, 473004 Nanyang, Henan, People's Republic of China, bDepartment of Chemical and Chemical Engineering, Guang Xi University, 530000 Nanning, Guangxi, People's Republic of China, and cLaiwu Steel Hospital, 271126 Laiwu, Shandong, People's Republic of China
*Correspondence e-mail: hyperchem@126.com
In the title compound, [Co(C8H5O4)(C9H6N7)]n, the divalent CoII atom is six-coordinated to three N atoms from two symmetrical 5-(pyridin-4-yl)-1H,2′H-3,3′-bi[1,2,4-triazole] (H2pyttz) ligands and three O atoms from three symmetrical 3-carboxybenzoate (Hbdic) ligands, leading to a distorted {CoN3O3} octahedral coordination environment. Two CoII cations are linked by four bridging carboxylate groups to generate a dinuclear [Co2(CO2)4] unit. The dinuclear units are further connected into a chain along [010] via the Hbdic ligands. The other infinite chain, along [100], is formed through the H2pyttz ligands. Finally, the two kinds of chains are cross-linked, by sharing the CoII cations, into a two-dimensional network. In the crystal, adjacent layers are further linked by O—H⋯N hydrogen bonds into a three-dimensional framework.
Keywords: crystal structure; cobalt complex; 5-(pyridin-4-yl)-1H,2′H-3,3′-bi(1,2,4-triazole); benzene-1,3-dicarboxylic acid; octahedral geometry; hydrogen bond.
CCDC reference: 1498228
1. Chemical context
In recent years, the design and synthesis of coordination polymers (CPs) or metal–organic frameworks (MOFs) have attracted great interest because of their fascinating architectures and potential applications in areas such as gas storage and separation, catalysis, fluorescence, magnetism, molecular recognition, conductivity etc (Kitagawa et al., 2004; Zhou et al., 2012; Cavka et al., 2014; Zhang et al., 2014; Huang et al., 2017; Nath et al., 2016; Ni et al., 2017; Yi et al., 2016; Sun et al., 2016). It is well known that organic ligands play a crucial role in the rational design and synthesis of coordination polymers (Li & Sato, 2017; Sun & Sun, 2015). Among the many organonitrogen ligands, the rigid 5-(pyridin-4-yl)-1H,2′H-3,3′-bi(1,2,4-triazole) ligand (H2pyttz) attracted our attention for the following reasons. First, the H2pyttz ligand possesses seven potential N-donor coordination sites and can exhibit various coordination modes. Second, the uncoordinated N atoms are helpful for the construction of hydrogen bonds. The hydrogen bonds not only increase the diversity of coordination polymer structures, but also enhance their stability. With an increasing interest in H2pyttz organometallic systems, we report herein on the synthesis and of the title compound [Co(C8H5O4)(C9H6N7)]n, (I).
2. Structural commentary
The contains one independent CoII cation, one partially deprotonated Hpyttz− ligand and one partial deprotonated Hbtc− ligand. Notably, the deprotonated Hbtc− ligand adopts two different coordination modes. The deprotonated carboxylate group has a bis(monodentate) coordination mode to bridge two CoII centers while the undeprotonated carboxylic group adopts a monodentate mode. As shown in Fig. 1, the CoII cation is six-coordinated to three carboxylic oxygen atoms from three symmetrical Hbtc− ligands and three nitrogen atoms from two symmetrical Hpyttz− ligands in a distorted [CoN3O3] octahedral coordination geometry. Four bridging carboxylate groups link two CoII cations to generate a dinuclear [Co2(CO2)4] unit, which is further connected into an infinite chain along the b-axis direction. There exist eight- and 16-membered metallamacrocycles in the chain structure. In the 16-membered metallamacrocycle, the dihedral angle between the two aromatic rings is 0°, indicating the parallel orientation of the two aromatic rings.
of (I)The other infinite linear chain is along the a-axis direction with a Co⋯Co distance of 6.5825 (5) Å and Co—Co—Co angle of 180.00° and it is also generated through the coordination between the Hpyttz− ligands and the CoII cations. In the complex, the Hpyttz− ligand is almost coplanar, with dihedral angles of 7.48 (4), 6.87 (4) and 4.43 (4) ° between the pyridine and the two triazole rings, respectively. Finally, these two kinds of chains are cross-linked, by sharing the CoII cations, into a two-dimensional network.
3. Supramolecular features
In the crystal, adjacent two-dimensional networks are packed parallel to each other in an ⋯AAAA⋯ fashion (Fig. 2). It should be noted that the carboxylic oxygen atom O3 and the uncoordinated nitrogen atom N7 in adjacent networks interact with each other and form strong O3—H3⋯N7 hydrogen bonds (Table 1), which further link the two-dimensional networks into a three-dimensional supramolecular architecture.
4. Database survey
A search of the Cambridge Structural Database (Version 5.37; Groom et al., 2016) for 5-(pyridin-4-yl)-1H,2′H-3,3′-bi(1,2,4-triazole) reveals five structures. Of these, there is only one CoII coordination structure (ZOTDIX; Gong et al., 2014). In this structure, the pyridyl nitrogen atom is not coordinated to the CoII cation.
5. Synthesis and crystallization
A mixture of Co(NO3)2.6H2O (0.10 mmol), 5-(pyridin-4-yl)-1H,2′H-3,3′-bi(1,2,4-triazole) (0.10 mmol), benzene-1,3-dicarboxylic acid (0.10 mmol) and H2O (10 ml) was stirred at room temperature for 30 min. When the pH value had been adjusted to about 7.0 with 0.1 M NaOH, the mixture was sealed in a 20 ml Tefon-lined stainless-steel reactor and then heated to 433 K for 72 h under autogenous pressure, and then slowly cooled to room temperature at a rate of 5 K h−1. Pink block-shaped crystals of the title complex were isolated, washed with distilled water, and dried in air (yield 52%).
6. Refinement
Crystal data, data collection and structure . H atoms attached to C and N atoms were placed in calculated positions (C—H = 0.93 Å, N—H = 0.86 Å) and refined as riding atoms with Uiso(H) = 1.2Ueq(C,N), respectively. The carboxyl H atom was located in the difference Fourier-map and refined isotropically with Uiso(H) = 1.5Ueq(O).
details are summarized in Table 2Supporting information
CCDC reference: 1498228
https://doi.org/10.1107/S205698901701533X/kq2016sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901701533X/kq2016Isup2.hkl
Data collection: SMART (Bruker, 2008); cell
SMART (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: DIAMOND (Brandenburg & Putz, 2006).[Co(C8H5O4)(C9H6N7)] | Z = 2 |
Mr = 436.26 | F(000) = 442 |
Triclinic, P1 | Dx = 1.825 Mg m−3 |
a = 6.5825 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0574 (12) Å | Cell parameters from 1163 reflections |
c = 13.9842 (12) Å | θ = 3.0–28.3° |
α = 74.214 (1)° | µ = 1.13 mm−1 |
β = 84.690 (2)° | T = 293 K |
γ = 82.303 (1)° | Block, pink |
V = 793.69 (14) Å3 | 0.20 × 0.18 × 0.15 mm |
Bruker SMART CCD area detector diffractometer | 2338 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.055 |
φ and ω scans | θmax = 28.4°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −8→8 |
Tmin = 0.797, Tmax = 0.858 | k = −11→12 |
5565 measured reflections | l = −16→18 |
3507 independent reflections |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: mixed |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0172P)2 + 0.0319P] where P = (Fo2 + 2Fc2)/3 |
3507 reflections | (Δ/σ)max < 0.001 |
265 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.59 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. |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.36855 (8) | 0.42648 (8) | 0.65379 (5) | 0.02024 (18) | |
N1 | 0.2335 (5) | 0.5770 (4) | 0.8362 (3) | 0.0196 (9) | |
N2 | 0.3746 (5) | 0.5162 (4) | 0.7767 (3) | 0.0182 (9) | |
N3 | 0.5482 (5) | 0.6182 (4) | 0.8697 (3) | 0.0210 (9) | |
N4 | 0.9301 (5) | 0.5039 (4) | 0.7413 (3) | 0.0200 (9) | |
H4 | 0.9832 | 0.5434 | 0.7811 | 0.024* | |
N5 | 1.0369 (5) | 0.4445 (4) | 0.6689 (3) | 0.0197 (9) | |
N6 | 0.7019 (5) | 0.4259 (4) | 0.6688 (3) | 0.0191 (9) | |
N7 | 0.0562 (5) | 0.8553 (5) | 1.1093 (3) | 0.0273 (10) | |
O1 | 0.3534 (4) | 0.3140 (4) | 0.5493 (2) | 0.0209 (7) | |
O2 | 0.6377 (4) | 0.3585 (4) | 0.4500 (2) | 0.0209 (7) | |
O3 | 0.8393 (5) | −0.0128 (4) | 0.2340 (3) | 0.0342 (10) | |
H3 | 0.917 (7) | −0.071 (6) | 0.200 (4) | 0.051* | |
O4 | 0.6280 (4) | −0.1888 (4) | 0.2391 (2) | 0.0257 (8) | |
C1 | 0.5576 (6) | 0.5438 (5) | 0.7995 (3) | 0.0180 (10) | |
C2 | 0.3424 (6) | 0.6368 (5) | 0.8906 (3) | 0.0199 (10) | |
C3 | 0.7332 (6) | 0.4911 (5) | 0.7405 (3) | 0.0173 (10) | |
C4 | 0.8918 (6) | 0.3997 (5) | 0.6277 (3) | 0.0206 (11) | |
H4A | 0.9183 | 0.3542 | 0.5751 | 0.025* | |
C5 | −0.0515 (6) | 0.7829 (6) | 1.0630 (4) | 0.0280 (12) | |
H5 | −0.1909 | 0.7793 | 1.0807 | 0.034* | |
C6 | 0.0347 (6) | 0.7140 (6) | 0.9909 (4) | 0.0282 (12) | |
H6 | −0.0461 | 0.6662 | 0.9598 | 0.034* | |
C7 | 0.2431 (6) | 0.7154 (5) | 0.9641 (3) | 0.0209 (10) | |
C8 | 0.3536 (6) | 0.7892 (6) | 1.0130 (4) | 0.0297 (12) | |
H8 | 0.4938 | 0.7923 | 0.9977 | 0.036* | |
C9 | 0.2573 (7) | 0.8578 (6) | 1.0842 (4) | 0.0300 (13) | |
H9 | 0.3342 | 0.9075 | 1.1159 | 0.036* | |
C10 | 0.4755 (6) | 0.2952 (5) | 0.4773 (3) | 0.0186 (10) | |
C11 | 0.6668 (6) | −0.0715 (6) | 0.2607 (3) | 0.0213 (10) | |
C12 | 0.4189 (6) | 0.1867 (5) | 0.4224 (3) | 0.0173 (10) | |
C13 | 0.5649 (6) | 0.1212 (5) | 0.3625 (3) | 0.0191 (10) | |
H13 | 0.6973 | 0.1499 | 0.3523 | 0.023* | |
C14 | 0.5117 (6) | 0.0126 (5) | 0.3179 (3) | 0.0198 (10) | |
C15 | 0.3112 (6) | −0.0227 (5) | 0.3286 (3) | 0.0235 (11) | |
H15 | 0.2761 | −0.0946 | 0.2982 | 0.028* | |
C16 | 0.1631 (6) | 0.0470 (6) | 0.3834 (4) | 0.0285 (12) | |
H16 | 0.0276 | 0.0257 | 0.3880 | 0.034* | |
C17 | 0.2189 (6) | 0.1497 (6) | 0.4316 (3) | 0.0239 (11) | |
H17 | 0.1206 | 0.1943 | 0.4706 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0155 (3) | 0.0282 (4) | 0.0212 (4) | −0.0045 (3) | 0.0037 (2) | −0.0142 (3) |
N1 | 0.0152 (18) | 0.027 (2) | 0.019 (2) | −0.0025 (16) | 0.0041 (15) | −0.0124 (19) |
N2 | 0.0152 (17) | 0.022 (2) | 0.019 (2) | −0.0014 (16) | 0.0029 (15) | −0.0101 (19) |
N3 | 0.0155 (18) | 0.028 (2) | 0.023 (2) | −0.0047 (16) | 0.0039 (15) | −0.0132 (19) |
N4 | 0.0158 (18) | 0.030 (2) | 0.019 (2) | −0.0041 (16) | 0.0025 (15) | −0.0150 (19) |
N5 | 0.0120 (17) | 0.024 (2) | 0.025 (2) | −0.0028 (16) | 0.0053 (15) | −0.0112 (19) |
N6 | 0.0159 (17) | 0.027 (2) | 0.019 (2) | −0.0039 (16) | 0.0009 (15) | −0.0129 (19) |
N7 | 0.031 (2) | 0.029 (3) | 0.025 (2) | −0.0022 (19) | 0.0044 (18) | −0.016 (2) |
O1 | 0.0245 (16) | 0.0234 (19) | 0.0183 (18) | −0.0064 (14) | 0.0066 (13) | −0.0120 (15) |
O2 | 0.0201 (15) | 0.0205 (18) | 0.0247 (19) | −0.0065 (13) | 0.0016 (13) | −0.0096 (16) |
O3 | 0.0267 (18) | 0.041 (2) | 0.043 (2) | −0.0092 (17) | 0.0161 (16) | −0.029 (2) |
O4 | 0.0300 (17) | 0.026 (2) | 0.026 (2) | −0.0057 (15) | 0.0039 (14) | −0.0147 (17) |
C1 | 0.018 (2) | 0.022 (3) | 0.016 (2) | −0.0021 (19) | 0.0014 (17) | −0.008 (2) |
C2 | 0.019 (2) | 0.025 (3) | 0.018 (3) | −0.006 (2) | 0.0003 (18) | −0.010 (2) |
C3 | 0.015 (2) | 0.020 (3) | 0.018 (2) | −0.0010 (18) | 0.0004 (17) | −0.008 (2) |
C4 | 0.017 (2) | 0.022 (3) | 0.026 (3) | 0.000 (2) | 0.0024 (19) | −0.014 (2) |
C5 | 0.020 (2) | 0.038 (3) | 0.027 (3) | −0.004 (2) | 0.010 (2) | −0.015 (3) |
C6 | 0.021 (2) | 0.042 (3) | 0.027 (3) | −0.003 (2) | 0.006 (2) | −0.021 (3) |
C7 | 0.025 (2) | 0.023 (3) | 0.017 (3) | 0.001 (2) | 0.0010 (19) | −0.011 (2) |
C8 | 0.017 (2) | 0.044 (3) | 0.034 (3) | −0.004 (2) | 0.003 (2) | −0.022 (3) |
C9 | 0.031 (3) | 0.037 (3) | 0.032 (3) | −0.009 (2) | 0.002 (2) | −0.024 (3) |
C10 | 0.016 (2) | 0.016 (3) | 0.023 (3) | 0.0015 (19) | 0.0000 (18) | −0.004 (2) |
C11 | 0.022 (2) | 0.026 (3) | 0.016 (3) | −0.001 (2) | −0.0006 (18) | −0.007 (2) |
C12 | 0.019 (2) | 0.023 (3) | 0.013 (2) | −0.0060 (19) | 0.0008 (17) | −0.010 (2) |
C13 | 0.016 (2) | 0.025 (3) | 0.019 (3) | −0.0109 (19) | 0.0068 (17) | −0.009 (2) |
C14 | 0.025 (2) | 0.019 (3) | 0.017 (2) | −0.004 (2) | 0.0040 (18) | −0.008 (2) |
C15 | 0.024 (2) | 0.026 (3) | 0.026 (3) | −0.008 (2) | 0.002 (2) | −0.016 (2) |
C16 | 0.021 (2) | 0.038 (3) | 0.033 (3) | −0.007 (2) | 0.003 (2) | −0.019 (3) |
C17 | 0.025 (2) | 0.027 (3) | 0.022 (3) | 0.002 (2) | 0.0048 (19) | −0.013 (2) |
Co1—O1 | 2.012 (3) | O4—C11 | 1.244 (5) |
Co1—O2i | 2.086 (3) | O4—Co1iii | 2.262 (4) |
Co1—N2 | 2.097 (3) | C1—C3 | 1.461 (5) |
Co1—N5ii | 2.162 (3) | C2—C7 | 1.463 (5) |
Co1—N6 | 2.223 (3) | C4—H4A | 0.9300 |
Co1—O4iii | 2.262 (4) | C5—C6 | 1.368 (5) |
N1—C2 | 1.347 (5) | C5—H5 | 0.9300 |
N1—N2 | 1.352 (4) | C6—C7 | 1.389 (6) |
N2—C1 | 1.345 (5) | C6—H6 | 0.9300 |
N3—C1 | 1.327 (5) | C7—C8 | 1.384 (6) |
N3—C2 | 1.357 (5) | C8—C9 | 1.377 (6) |
N4—C3 | 1.318 (5) | C8—H8 | 0.9300 |
N4—N5 | 1.368 (4) | C9—H9 | 0.9300 |
N4—H4 | 0.8600 | C10—C12 | 1.502 (5) |
N5—C4 | 1.320 (5) | C11—C14 | 1.495 (5) |
N5—Co1iv | 2.162 (3) | C12—C17 | 1.387 (6) |
N6—C3 | 1.338 (5) | C12—C13 | 1.395 (5) |
N6—C4 | 1.345 (5) | C13—C14 | 1.394 (5) |
N7—C5 | 1.339 (5) | C13—H13 | 0.9300 |
N7—C9 | 1.339 (5) | C14—C15 | 1.385 (5) |
O1—C10 | 1.262 (5) | C15—C16 | 1.377 (5) |
O2—C10 | 1.258 (5) | C15—H15 | 0.9300 |
O2—Co1i | 2.086 (3) | C16—C17 | 1.391 (6) |
O3—C11 | 1.299 (5) | C16—H16 | 0.9300 |
O3—H3 | 0.89 (5) | C17—H17 | 0.9300 |
O1—Co1—O2i | 93.18 (12) | N5—C4—N6 | 113.9 (4) |
O1—Co1—N2 | 172.28 (15) | N5—C4—H4A | 123.1 |
O2i—Co1—N2 | 94.31 (13) | N6—C4—H4A | 123.1 |
O1—Co1—N5ii | 87.27 (12) | N7—C5—C6 | 122.8 (4) |
O2i—Co1—N5ii | 91.64 (13) | N7—C5—H5 | 118.6 |
N2—Co1—N5ii | 90.64 (12) | C6—C5—H5 | 118.6 |
O1—Co1—N6 | 105.23 (11) | C5—C6—C7 | 119.9 (4) |
O2i—Co1—N6 | 90.18 (13) | C5—C6—H6 | 120.1 |
N2—Co1—N6 | 76.64 (12) | C7—C6—H6 | 120.1 |
N5ii—Co1—N6 | 167.25 (12) | C8—C7—C6 | 116.9 (4) |
O1—Co1—O4iii | 84.32 (12) | C8—C7—C2 | 121.6 (4) |
O2i—Co1—O4iii | 177.47 (11) | C6—C7—C2 | 121.4 (4) |
N2—Co1—O4iii | 88.17 (13) | C9—C8—C7 | 120.4 (4) |
N5ii—Co1—O4iii | 87.82 (13) | C9—C8—H8 | 119.8 |
N6—Co1—O4iii | 90.88 (13) | C7—C8—H8 | 119.8 |
C2—N1—N2 | 105.2 (3) | N7—C9—C8 | 122.0 (4) |
C1—N2—N1 | 105.6 (3) | N7—C9—H9 | 119.0 |
C1—N2—Co1 | 117.7 (3) | C8—C9—H9 | 119.0 |
N1—N2—Co1 | 136.0 (2) | O2—C10—O1 | 125.2 (4) |
C1—N3—C2 | 100.7 (3) | O2—C10—C12 | 119.0 (4) |
C3—N4—N5 | 109.5 (3) | O1—C10—C12 | 115.8 (4) |
C3—N4—H4 | 125.2 | O4—C11—O3 | 123.0 (4) |
N5—N4—H4 | 125.2 | O4—C11—C14 | 121.0 (4) |
C4—N5—N4 | 103.0 (3) | O3—C11—C14 | 116.1 (4) |
C4—N5—Co1iv | 135.8 (3) | C17—C12—C13 | 119.2 (4) |
N4—N5—Co1iv | 121.0 (2) | C17—C12—C10 | 119.8 (4) |
C3—N6—C4 | 103.5 (3) | C13—C12—C10 | 121.0 (4) |
C3—N6—Co1 | 111.1 (2) | C14—C13—C12 | 119.8 (4) |
C4—N6—Co1 | 144.9 (3) | C14—C13—H13 | 120.1 |
C5—N7—C9 | 118.1 (4) | C12—C13—H13 | 120.1 |
C10—O1—Co1 | 132.1 (3) | C15—C14—C13 | 119.8 (4) |
C10—O2—Co1i | 120.5 (3) | C15—C14—C11 | 118.3 (4) |
C11—O3—H3 | 108 (3) | C13—C14—C11 | 121.9 (4) |
C11—O4—Co1iii | 124.8 (3) | C16—C15—C14 | 120.9 (4) |
N3—C1—N2 | 114.7 (3) | C16—C15—H15 | 119.5 |
N3—C1—C3 | 130.7 (4) | C14—C15—H15 | 119.5 |
N2—C1—C3 | 114.6 (3) | C15—C16—C17 | 119.1 (4) |
N1—C2—N3 | 113.8 (3) | C15—C16—H16 | 120.5 |
N1—C2—C7 | 121.9 (4) | C17—C16—H16 | 120.5 |
N3—C2—C7 | 124.3 (4) | C12—C17—C16 | 121.1 (4) |
N4—C3—N6 | 110.1 (3) | C12—C17—H17 | 119.5 |
N4—C3—C1 | 130.3 (4) | C16—C17—H17 | 119.5 |
N6—C3—C1 | 119.5 (3) | ||
C2—N1—N2—C1 | −0.1 (5) | N1—C2—C7—C8 | −173.9 (5) |
C2—N1—N2—Co1 | −169.6 (4) | N3—C2—C7—C8 | 5.4 (8) |
C3—N4—N5—C4 | 0.5 (5) | N1—C2—C7—C6 | 8.8 (7) |
C3—N4—N5—Co1iv | −174.9 (3) | N3—C2—C7—C6 | −171.9 (5) |
C2—N3—C1—N2 | −0.1 (5) | C6—C7—C8—C9 | −0.4 (8) |
C2—N3—C1—C3 | 177.7 (5) | C2—C7—C8—C9 | −177.8 (5) |
N1—N2—C1—N3 | 0.1 (5) | C5—N7—C9—C8 | 0.2 (8) |
Co1—N2—C1—N3 | 171.9 (3) | C7—C8—C9—N7 | 0.5 (8) |
N1—N2—C1—C3 | −178.1 (4) | Co1i—O2—C10—O1 | −88.9 (5) |
Co1—N2—C1—C3 | −6.3 (5) | Co1i—O2—C10—C12 | 91.8 (4) |
N2—N1—C2—N3 | 0.0 (5) | Co1—O1—C10—O2 | −6.3 (7) |
N2—N1—C2—C7 | 179.3 (4) | Co1—O1—C10—C12 | 173.1 (3) |
C1—N3—C2—N1 | 0.1 (5) | Co1iii—O4—C11—O3 | 104.3 (5) |
C1—N3—C2—C7 | −179.3 (5) | Co1iii—O4—C11—C14 | −77.2 (5) |
N5—N4—C3—N6 | −0.6 (5) | O2—C10—C12—C17 | −162.0 (4) |
N5—N4—C3—C1 | −176.6 (5) | O1—C10—C12—C17 | 18.6 (6) |
C4—N6—C3—N4 | 0.4 (5) | O2—C10—C12—C13 | 18.4 (7) |
Co1—N6—C3—N4 | −173.6 (3) | O1—C10—C12—C13 | −161.0 (4) |
C4—N6—C3—C1 | 177.0 (4) | C17—C12—C13—C14 | −4.1 (7) |
Co1—N6—C3—C1 | 3.0 (5) | C10—C12—C13—C14 | 175.5 (4) |
N3—C1—C3—N4 | −0.2 (9) | C12—C13—C14—C15 | 3.9 (7) |
N2—C1—C3—N4 | 177.7 (5) | C12—C13—C14—C11 | −174.3 (4) |
N3—C1—C3—N6 | −175.9 (5) | O4—C11—C14—C15 | −13.1 (7) |
N2—C1—C3—N6 | 1.9 (6) | O3—C11—C14—C15 | 165.5 (4) |
N4—N5—C4—N6 | −0.2 (5) | O4—C11—C14—C13 | 165.1 (5) |
Co1iv—N5—C4—N6 | 174.1 (3) | O3—C11—C14—C13 | −16.3 (7) |
C3—N6—C4—N5 | −0.1 (5) | C13—C14—C15—C16 | −0.6 (7) |
Co1—N6—C4—N5 | 170.1 (4) | C11—C14—C15—C16 | 177.7 (4) |
C9—N7—C5—C6 | −0.9 (8) | C14—C15—C16—C17 | −2.5 (7) |
N7—C5—C6—C7 | 1.0 (8) | C13—C12—C17—C16 | 1.0 (7) |
C5—C6—C7—C8 | −0.3 (7) | C10—C12—C17—C16 | −178.6 (5) |
C5—C6—C7—C2 | 177.1 (5) | C15—C16—C17—C12 | 2.3 (8) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y, −z+1; (iv) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N7v | 0.89 (5) | 1.72 (5) | 2.592 (4) | 166 (5) |
Symmetry code: (v) x+1, y−1, z−1. |
Funding information
We acknowledge financial support from Henan Province Project Education Fund (17 A430027).
References
Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cavka, J. H., Grande, C. A., Mondino, G. & Blom, R. (2014). Ind. Eng. Chem. Res. 53, 15500–15507. Web of Science CrossRef CAS
Gong, Y., Yang, Y. X., Zhang, P., Gao, X. L., Yin, J. L. & Lin, J. H. (2014). Dalton Trans. 43, 16928–16936. CSD CrossRef CAS PubMed
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals
Huang, Y.-B., Liang, J., Wang, X.-S. & Cao, R. (2017). Chem. Soc. Rev. 46, 126–157. CrossRef CAS PubMed
Kitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334–2375. Web of Science CrossRef CAS
Li, G.-L. & Sato, O. (2017). Acta Cryst. E73, 993–995. CSD CrossRef IUCr Journals
Nath, I., Chakraborty, J. & Verpoort, F. (2016). Chem. Soc. Rev. 45, 4127–4170. CrossRef CAS PubMed
Ni, Z.-P., Liu, J.-L., Hoque, Md. N., Liu, W., Li, J.-Y., Chen, Y.-C. & Tong, M.-L. (2017). Chem. Rev. 335, 28–43. CAS
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals
Sun, L., Campbell, M. G. & Dincă, M. (2016). Angew. Chem. Int. Ed. 55, 3566–3579. CrossRef CAS
Sun, Y.-X. & Sun, W.-Y. (2015). CrystEngComm, 17, 4045–4063. CrossRef CAS
Yi, F.-Y., Chen, D., Wu, M.-K., Han, L. & Jiang, H.-L. (2016). ChemPlusChem, 81, 675–690. CrossRef CAS
Zhang, Z., Yao, Z.-Z., Xiang, S. C. & Chen, B. L. (2014). Energ. Environ. Sci. 7, 2868–2899. CrossRef CAS
Zhou, H. C., Long, J. R. & Yaghi, O. M. (2012). Chem. Rev. 112, 673–674. Web of Science CrossRef CAS PubMed
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.