Poly[[μ3-2-(benzotriazol-1-yl)acetato-κ3O:O′:N3]chlorido­(ethanol-κO)cobalt(II)]

Zheng, Y.-Y.; Su, D.-S.; Yao, Q.-H.; Huang, M.-M.

doi:10.1107/S2414314624006308

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 7| July 2024| x240630

https://doi.org/10.1107/S2414314624006308

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Poly[[μ₃-2-(benzotriazol-1-yl)acetato-κ³O:O′:N³]chlorido(ethanol-κO)cobalt(II)]

Yun-Yun Zheng,^a ^* De-Sen Su,^a Qing-Hua Yao ^a and Min-Min Huang ^a

^aFujian Key Laboratory of Agro-Products Quality and Safety, Institute of Quality Standards Testing Technology for Agro-products, Fujian Academy of Agricultural Sciences, 247 Wu-Si Rd, Fuzhou, People's Republic of China
^*Correspondence e-mail: yyzheng@xmu.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 6 June 2024; accepted 27 June 2024; online 5 July 2024)

In the title compound, [Co(C₈H₆N₃O₂)Cl(C₂H₅OH)]_n, the Co^II atoms adopt octahedral trans-CoN₂O₄ and tetrahedral CoCl₂O₂ coordination geometries (site symmetries $[\overline{1}]$ and m, respectively). The bridging μ₃-O:O:N 2-(benzotriazol-1-yl)acetato ligands connect the octahedral cobalt nodes into (010) sheets and the CoCl₂ fragments link the sheets into a tri-periodic network. The structure displays O—H⋯O hydrogen bonding and the ethanol molecule is disordered over two orientations.

Keywords: 2-(benzotriazol-1-yl) acetic acid; cobalt; coordination polymers; crystal structure.

CCDC reference: 2366143

Structure description

As a ligand with multiple coordination sites, benzotriazole is a good linker in the generation of metal–organic frameworks (MOFs) as it can bridge different metal cations to afford coordination polymers that exhibit structural diversity and facile accessibility of functionalized new magnetic materials (Bai et al., 2008 ; Shao et al., 2008 ; Müller-Buschbaum & Mokaddem, 2006 ). Functional groups such as carboxylate, hydroxy and pyridyl can be added to the benzotriazole core, increasing its coordination possibilities (Stoumpos et al., 2008 ; Zhang et al., 2007 ; Hu et al., 2008 ; Hang & Ye, 2008 ). 1H-Benzotriazole-1-acetic acid (Hbtaa), a flexible ligand, containing a carboxylate group (when deprotonated) and a triazole unit has been used to construct MOFs (Zheng et al., 2010 ; Zeng, 2013 ). As part of our work in this area, we now report the synthesis and crystal structure of the title coordination polymer, [Co(C₈H₆N₃O₂)Cl(C₂H₅OH)]_n, where C₈H₆N₃O₂⁻ (L⁻) is the 2-benzotriazol-1-yl)acetate anion.

Single-crystal structural analysis reveals that the asymmetric unit consists of two Co^II cations (one with site symmetry m and one with site symmetry $[\overline{1}]$ ), one L⁻ ligand, two chloride ions (both site symmetry m) and one disordered ethanol molecule (Fig. 1). Co1 is four-coordinated by two L⁻ ligands in O-monodentate mode and two μ¹-chloride ions in a tetrahedral coordination geometry, whereas Co2 is six-coordinated by four L⁻ ligands (two in N-monodentate mode and two in O-monodentate mode) and two ethanol molecules. In the extended structure, the μ³-O,O,N bridging L⁻ ligand links the Co2 nodes into (010) sheets (Fig. 2) and the Co1Cl₂ fragments link the sheets into a tri-periodic network (Fig. 3). An O—H⋯O hydrogen bond (Table 1) occurs.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1	0.86 (1)	2.01 (2)	2.734 (3)	141 (2)

Figure 1
The asymmetric unit of the title compound showing 50% displacement ellipsoids. Only one orientation of the disordered ethanol molecule is shown.

Figure 2
Part of a (010) sheet in the title compound.

Figure 3
The three-dimensional network in the title compound.

Synthesis and crystallization

CoCl₂ (1.00 mmol) and 2-(benzotriazol-1-yl) acetic acid (1.00 mmol) were mixed in 10.0 ml of ethanol with stirring for about 30 min at room temperature. Blue block-shaped crystals of the title compound were collected by filtration in 40% yield. Analysis (%) calculated (Found) for C₁₀H₁₂O₃N₃ClCo: C, 37.94 (37.72); H, 3.82 (3.89); N, 13.27 (13.32).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Co(C₈H₆N₃O₂)Cl(C₂H₅OH)]
M_r	316.61
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	223
a, b, c (Å)	9.681 (2), 18.411 (4), 13.163 (3)
V (Å³)	2346.1 (9)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	1.69
Crystal size (mm)	0.25 × 0.15 × 0.09

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.745, 0.859
No. of measured, independent and observed [I > 2σ(I)] reflections	13580, 3058, 2337
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.120, 1.09
No. of reflections	3058
No. of parameters	184
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.38
Computer programs: SMART and SAINT (Bruker, 2002 ), SHELXD1997 and SHELXL (Sheldrick, 2008 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2366143

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624006308/hb4477sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624006308/hb4477Isup2.hkl

checkCIF report

Computing details top

Poly[[µ₃-2-(benzotriazol-1-yl)acetato-κ³O:O':N³]chlorido(ethanol-κO)cobalt(II)] top

Crystal data top

[Co(C₈H₆N₃O₂)Cl(C₂H₆O)]	D_x = 1.793 Mg m⁻³
M_r = 316.61	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 39979 reflections
a = 9.681 (2) Å	θ = 2.6–27.6°
b = 18.411 (4) Å	µ = 1.69 mm⁻¹
c = 13.163 (3) Å	T = 223 K
V = 2346.1 (9) Å³	Block, blue
Z = 8	0.25 × 0.15 × 0.09 mm
F(000) = 1288

Data collection top

Bruker SMART CCD diffractometer	2337 reflections with I > 2σ(I)
ω scans	R_int = 0.037
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.5°, θ_min = 1.9°
T_min = 0.745, T_max = 0.859	h = −12→13
13580 measured reflections	k = −23→24
3058 independent reflections	l = −11→17

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0582P)² + 2.3224P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
3058 reflections	Δρ_max = 0.71 e Å⁻³
184 parameters	Δρ_min = −0.38 e Å⁻³
3 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Co1	0.43288 (6)	0.2500	0.34271 (4)	0.03019 (17)
Co2	0.5000	0.5000	0.5000	0.02529 (16)
Cl1	0.34331 (13)	0.2500	0.18726 (8)	0.0404 (3)
Cl2	0.27129 (14)	0.2500	0.46492 (10)	0.0472 (3)
O1	0.5318 (2)	0.33968 (11)	0.37700 (15)	0.0296 (4)
O2	0.5907 (2)	0.45529 (11)	0.36795 (15)	0.0288 (4)
O3	0.4442 (3)	0.40048 (12)	0.55516 (16)	0.0404 (6)
H3	0.448 (4)	0.3656 (8)	0.5120 (12)	0.061*
N1	0.6491 (2)	0.44636 (13)	0.16425 (17)	0.0279 (5)
N2	0.7812 (3)	0.44389 (13)	0.13833 (18)	0.0303 (5)
N3	0.8091 (3)	0.50073 (13)	0.08376 (18)	0.0296 (5)
C1	0.5701 (3)	0.39542 (15)	0.3296 (2)	0.0245 (6)
C2	0.4659 (6)	0.3692 (2)	0.6509 (3)	0.0657 (13)
H2AA	0.4721	0.4093	0.6986	0.079*	0.507 (11)
H2AB	0.3817	0.3432	0.6674	0.079*	0.507 (11)
H2BC	0.5343	0.3314	0.6415	0.079*	0.493 (11)
H2BD	0.5090	0.4063	0.6925	0.079*	0.493 (11)
C3	0.5741 (13)	0.3227 (7)	0.6741 (10)	0.095 (4)	0.507 (11)
H3A	0.6599	0.3487	0.6695	0.143*	0.507 (11)
H3B	0.5747	0.2829	0.6270	0.143*	0.507 (11)
H3C	0.5626	0.3045	0.7419	0.143*	0.507 (11)
C4	0.5894 (3)	0.38538 (16)	0.2171 (2)	0.0303 (6)
H4A	0.6480	0.3433	0.2062	0.036*
H4B	0.5002	0.3748	0.1870	0.036*
C5	0.6926 (3)	0.54205 (16)	0.0755 (2)	0.0297 (6)
C6	0.5883 (3)	0.50689 (16)	0.1263 (2)	0.0303 (6)
C7	0.4538 (3)	0.5326 (2)	0.1284 (3)	0.0388 (7)
H7	0.3835	0.5079	0.1619	0.047*
C8	0.4311 (4)	0.5955 (2)	0.0789 (3)	0.0464 (9)
H8	0.3422	0.6146	0.0776	0.056*
C9	0.5380 (4)	0.6334 (2)	0.0290 (3)	0.0446 (8)
H9	0.5181	0.6775	−0.0022	0.053*
C10	0.6678 (4)	0.60771 (17)	0.0254 (2)	0.0389 (7)
H10	0.7376	0.6324	−0.0087	0.047*
C3A	0.3657 (10)	0.3405 (5)	0.7065 (6)	0.061 (3)	0.493 (11)
H3AA	0.3169	0.3050	0.6670	0.092*	0.493 (11)
H3AB	0.3030	0.3781	0.7272	0.092*	0.493 (11)
H3AC	0.4047	0.3178	0.7655	0.092*	0.493 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0432 (4)	0.0220 (3)	0.0254 (3)	0.000	0.0007 (2)	0.000
Co2	0.0336 (3)	0.0231 (3)	0.0191 (3)	−0.0040 (2)	−0.0011 (2)	−0.0030 (2)
Cl1	0.0500 (7)	0.0401 (6)	0.0310 (6)	0.000	−0.0062 (5)	0.000
Cl2	0.0544 (7)	0.0450 (7)	0.0423 (6)	0.000	0.0154 (6)	0.000
O1	0.0409 (11)	0.0250 (10)	0.0230 (10)	−0.0056 (9)	0.0008 (9)	0.0008 (8)
O2	0.0389 (11)	0.0259 (10)	0.0217 (9)	−0.0043 (8)	0.0033 (8)	−0.0050 (8)
O3	0.0704 (16)	0.0263 (11)	0.0245 (11)	−0.0106 (11)	−0.0037 (11)	−0.0014 (9)
N1	0.0327 (12)	0.0291 (12)	0.0220 (11)	−0.0024 (10)	0.0040 (10)	0.0015 (9)
N2	0.0369 (13)	0.0287 (12)	0.0252 (12)	0.0001 (11)	0.0060 (10)	0.0035 (10)
N3	0.0351 (13)	0.0273 (12)	0.0265 (12)	−0.0005 (10)	0.0046 (11)	0.0059 (10)
C1	0.0249 (13)	0.0263 (14)	0.0223 (13)	0.0001 (11)	−0.0018 (11)	0.0015 (10)
C2	0.112 (4)	0.047 (2)	0.038 (2)	−0.001 (2)	−0.014 (2)	0.0075 (18)
C3	0.111 (10)	0.079 (8)	0.096 (9)	0.013 (7)	−0.004 (7)	0.027 (6)
C4	0.0430 (16)	0.0242 (13)	0.0238 (13)	−0.0065 (12)	0.0059 (12)	−0.0004 (11)
C5	0.0386 (16)	0.0295 (14)	0.0210 (13)	−0.0006 (12)	0.0021 (12)	0.0013 (11)
C6	0.0385 (15)	0.0307 (15)	0.0217 (13)	0.0012 (12)	0.0007 (12)	−0.0015 (11)
C7	0.0369 (16)	0.0463 (19)	0.0332 (17)	0.0021 (15)	0.0027 (14)	−0.0039 (15)
C8	0.047 (2)	0.054 (2)	0.0388 (19)	0.0146 (17)	−0.0046 (16)	−0.0047 (16)
C9	0.062 (2)	0.0367 (18)	0.0351 (18)	0.0117 (16)	−0.0053 (16)	0.0043 (15)
C10	0.055 (2)	0.0334 (16)	0.0281 (15)	0.0023 (15)	0.0004 (15)	0.0046 (13)
C3A	0.082 (6)	0.069 (6)	0.033 (4)	−0.019 (5)	0.003 (4)	0.007 (4)

Geometric parameters (Å, º) top

Co1—Cl1	2.2223 (13)	C2—H2BC	0.9700
Co1—Cl2	2.2439 (14)	C2—H2BD	0.9700
Co1—O1ⁱ	1.961 (2)	C2—C3	1.387 (12)
Co1—O1	1.961 (2)	C2—C3A	1.324 (9)
Co2—O2	2.114 (2)	C3—H3A	0.9600
Co2—O2ⁱⁱ	2.114 (2)	C3—H3B	0.9600
Co2—O3ⁱⁱ	2.043 (2)	C3—H3C	0.9600
Co2—O3	2.043 (2)	C4—H4A	0.9700
Co2—N3ⁱⁱⁱ	2.152 (3)	C4—H4B	0.9700
Co2—N3^iv	2.152 (3)	C5—C6	1.373 (4)
O1—C1	1.257 (3)	C5—C10	1.397 (4)
O2—C1	1.228 (3)	C6—C7	1.386 (5)
O3—H3	0.859 (9)	C7—H7	0.9300
O3—C2	1.401 (4)	C7—C8	1.347 (5)
N1—N2	1.324 (3)	C8—H8	0.9300
N1—C4	1.441 (4)	C8—C9	1.410 (5)
N1—C6	1.356 (4)	C9—H9	0.9300
N2—N3	1.298 (3)	C9—C10	1.344 (5)
N3—Co2^v	2.152 (2)	C10—H10	0.9300
N3—C5	1.365 (4)	C3A—H3AA	0.9600
C1—C4	1.505 (4)	C3A—H3AB	0.9600
C2—H2AA	0.9700	C3A—H3AC	0.9600
C2—H2AB	0.9700

Cl1—Co1—Cl2	112.83 (6)	C3—C2—O3	124.4 (7)
O1—Co1—Cl1	113.73 (6)	C3—C2—H2AA	106.2
O1ⁱ—Co1—Cl1	113.73 (6)	C3—C2—H2AB	106.2
O1—Co1—Cl2	100.10 (7)	C3A—C2—O3	123.4 (6)
O1ⁱ—Co1—Cl2	100.10 (7)	C3A—C2—H2BC	106.5
O1—Co1—O1ⁱ	114.66 (13)	C3A—C2—H2BD	106.5
O2ⁱⁱ—Co2—O2	180.0	C2—C3—H3A	109.5
O2ⁱⁱ—Co2—N3ⁱⁱⁱ	93.56 (9)	C2—C3—H3B	109.5
O2—Co2—N3ⁱⁱⁱ	86.44 (9)	C2—C3—H3C	109.5
O2ⁱⁱ—Co2—N3^iv	86.44 (9)	H3A—C3—H3B	109.5
O2—Co2—N3^iv	93.56 (9)	H3A—C3—H3C	109.5
O3—Co2—O2	93.03 (8)	H3B—C3—H3C	109.5
O3ⁱⁱ—Co2—O2ⁱⁱ	93.03 (8)	N1—C4—C1	115.4 (2)
O3ⁱⁱ—Co2—O2	86.97 (8)	N1—C4—H4A	108.4
O3—Co2—O2ⁱⁱ	86.97 (8)	N1—C4—H4B	108.4
O3ⁱⁱ—Co2—O3	180.0	C1—C4—H4A	108.4
O3—Co2—N3ⁱⁱⁱ	87.74 (10)	C1—C4—H4B	108.4
O3—Co2—N3^iv	92.26 (10)	H4A—C4—H4B	107.5
O3ⁱⁱ—Co2—N3ⁱⁱⁱ	92.25 (10)	N3—C5—C6	107.8 (2)
O3ⁱⁱ—Co2—N3^iv	87.75 (10)	N3—C5—C10	131.4 (3)
N3ⁱⁱⁱ—Co2—N3^iv	180.0	C6—C5—C10	120.8 (3)
C1—O1—Co1	135.83 (19)	N1—C6—C5	104.4 (3)
C1—O2—Co2	128.27 (18)	N1—C6—C7	133.0 (3)
Co2—O3—H3	115.0 (14)	C5—C6—C7	122.6 (3)
C2—O3—Co2	130.4 (2)	C6—C7—H7	122.0
C2—O3—H3	106.3 (14)	C8—C7—C6	115.9 (3)
N2—N1—C4	119.0 (2)	C8—C7—H7	122.0
N2—N1—C6	110.6 (2)	C7—C8—H8	119.0
C6—N1—C4	130.1 (3)	C7—C8—C9	122.1 (3)
N3—N2—N1	108.4 (2)	C9—C8—H8	119.0
N2—N3—Co2^v	117.20 (19)	C8—C9—H9	119.0
N2—N3—C5	108.8 (2)	C10—C9—C8	121.9 (3)
C5—N3—Co2^v	132.23 (19)	C10—C9—H9	119.0
O1—C1—C4	115.1 (2)	C5—C10—H10	121.7
O2—C1—O1	125.2 (3)	C9—C10—C5	116.6 (3)
O2—C1—C4	119.6 (2)	C9—C10—H10	121.7
O3—C2—H2AA	106.2	C2—C3A—H3AA	109.5
O3—C2—H2AB	106.2	C2—C3A—H3AB	109.5
O3—C2—H2BC	106.5	C2—C3A—H3AC	109.5
O3—C2—H2BD	106.5	H3AA—C3A—H3AB	109.5
H2AA—C2—H2AB	106.4	H3AA—C3A—H3AC	109.5
H2BC—C2—H2BD	106.5	H3AB—C3A—H3AC	109.5

Co1—O1—C1—O2	154.9 (2)	N2—N3—C5—C10	−179.9 (3)
Co1—O1—C1—C4	−24.5 (4)	N3—C5—C6—N1	1.1 (3)
Co2—O2—C1—O1	−27.3 (4)	N3—C5—C6—C7	−176.7 (3)
Co2—O2—C1—C4	152.1 (2)	N3—C5—C10—C9	177.7 (3)
Co2—O3—C2—C3	−96.0 (8)	C4—N1—N2—N3	174.0 (2)
Co2—O3—C2—C3A	127.9 (6)	C4—N1—C6—C5	−174.1 (3)
Co2^v—N3—C5—C6	162.5 (2)	C4—N1—C6—C7	3.3 (5)
Co2^v—N3—C5—C10	−16.0 (5)	C5—C6—C7—C8	−1.3 (5)
O1—C1—C4—N1	−172.8 (3)	C6—N1—N2—N3	−0.5 (3)
O2—C1—C4—N1	7.8 (4)	C6—N1—C4—C1	−84.3 (4)
N1—N2—N3—Co2^v	−165.54 (18)	C6—C5—C10—C9	−0.7 (5)
N1—N2—N3—C5	1.1 (3)	C6—C7—C8—C9	−0.8 (5)
N1—C6—C7—C8	−178.3 (3)	C7—C8—C9—C10	2.1 (6)
N2—N1—C4—C1	102.4 (3)	C8—C9—C10—C5	−1.3 (5)
N2—N1—C6—C5	−0.4 (3)	C10—C5—C6—N1	179.8 (3)
N2—N1—C6—C7	177.0 (3)	C10—C5—C6—C7	2.0 (5)
N2—N3—C5—C6	−1.4 (3)

Symmetry codes: (i) x, −y+1/2, z; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, y, −z+1/2; (iv) −x+3/2, −y+1, z+1/2; (v) −x+3/2, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.86 (1)	2.01 (2)	2.734 (3)	141 (2)

Funding information

Funding for this research was provided by: the Program for Public Welfare Sciedtific Research Institute in Fujian Province (grant No. 2020R1022003); the Project for Youth Innovation Team in Fujian Academy of Agricultural Sciences (grant No. STIT 2021011-3); Collaborative innovation project in Fujian Province (grant No. XTCXGC2021020).

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