Poly[(μ3-5-hy­droxy­isophthalato)[μ2-1,1′-(1,4-phenyl­ene)bis­(1H-imidazole)]­copper]

Tao, H.-H.; Chen, Y.-H.; Liu, Y.-S.; Deji, Z.-G.

doi:10.1107/S2414314616018022

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 11| November 2016| x161802

https://doi.org/10.1107/S2414314616018022

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Poly[(μ₃-5-hydroxyisophthalato)[μ₂-1,1′-(1,4-phenylene)bis(1H-imidazole)]copper]

Hong-Hong Tao,^a ^* Yu-Han Chen,^a Ya-Sai Liu ^a and Zhuo-Ga Deji ^a

^aPeople's Hospital of Tibet Autonomic Region, Lasa 850000, People's Republic of China
^*Correspondence e-mail: taohonghong01@163.com

Edited by A. J. Lough, University of Toronto, Canada (Received 20 October 2016; accepted 9 November 2016; online 15 November 2016)

The title compound, [Cu(C₈H₄O₅)(C₁₂H₁₀N₄)]_n, was obtained by the reaction of copper(II) nitrate hydrate, with the OH-BDC organic linker and bib molecules [OH-BDC = 5-hydroxyisophthalic acid and bib = 1,4-bis(imidazol-1-yl)benzene]. The asymmetric unit comprises one Cu^II cation, one OH-BDC⁻² dianion and a bib ligand. The Cu^II ion is coordinated by three carboxylate O atoms and two bib-N atoms, all from bridging ligands, to form a slightly distorted trigonal–bipyramidal geometry. The Cu^II ions are bridged by OH-BDC⁻² ligands, forming a chain along the [100] direction; the chains are connected by bib molecules to form a two-dimensional net. In topological terms, considering the Cu^II atoms as nodes and the OH-BDC⁻² ligands as linkers, the two-dimensional structure can be simplified as a typical 2-nodal 3,5 L2 plane network. The crystal structure features O—H⋯O hydrogen bonds between OH-BDC⁻² anions, resulting in a three-dimensional supramolecular network.

Keywords: crystal structure; Cu-based; mixed ligands; hydrogen bonding; 3,5 L2 topology..

CCDC reference: 1515776

Structure description

A variety of metal–organic frameworks with intertesting structures have been reported based on 5-hydroxyisophthalic acid as this kind of carboxylate ligand offers six kinds of intricate connection models (Xu & Li, 2014 ). Supermolecules constructed by mixed ligands including carboxylate ligands and other N-donor molecules often show interesting networks compared with those compounds constructed by a single ligand (Xu et al., 2015 ). However, there are only a few examples reported which are based on OH-BDC and bib molecules (Wang et al., 2014 ; Liu & Guo., 2012 ; Su et al., 2015 ; Li et al. 2015 ; Guo et al., 2013 ). For this synthesis, we selected OH-BDC, bib organic ligands and copper(II) to construct a new supermolecule and present herein the structure of the title compound (Fig. 1), which is isostructural with the Mn^II-based analogue, (Li et al., 2015).

Figure 1
The asymmetric unit of the title compound, showing some symmetry-related atoms. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) x − 1, y + 1, z − 1; (ii) x + 1, y,z; (iii) −x + 1, −y + 2, −z + 1; (iv) x − 1, y, z; (v) x + 1, y − 1, z + 1.]

The Cu^II ion is coordinated by three carboxylate O atoms and two bib-N atoms, all from bridging ligands, to form a slightly distorted trigonal–bipyramidal geometry. The Cu^II ions are bridged by OH-BDC⁻² ligands, forming a chain along the [100] direction; the chains are connected by bib molecules to form a two-dimensional net. In topological terms, considering the Cu^II atoms as nodes and the OH-BDC⁻² ligands as linkers, the two-dimensional structure can be simplified as a typical 2-nodal 3,5 L2 plane network.

The crystal structure features O—H⋯O hydrogen bonds (Table 1) between OH-BDC⁻² anions, resulting in a three-dimensional supramolecular network (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O4ⁱ	0.82	1.84	2.660 (4)	177
Symmetry code: (i) -x, -y+2, -z.

Figure 2
The crystal packing of the title complex, viewed along the b axis, with O—H hydrogen bonds shown as dashed lines.

Synthesis and crystallization

The title complex was synthesized by the reaction of 5-hydroxyisophthalic (9.1 mg, 0.05 mmol), 1,4-bis(1-imidazolyl)benzene (10.5 mg, 0.05 mmol) in 8 ml of deionized water with copper(II) nitrate hydrate (24.1 mg, 0.1 mmol) in 20 ml of methanol and the mixture was refluxed for 0.5 h. To the above mixture, 0.5 ml of formic acid was added and the resulting fluid was placed in a Teflon-lined stainless-steel reactor. The reactor was heated to 413 K for 72 h. It was then cooled to room temperature. Blue block-shaped crystals were isolated in 68% yield (based on the OH-BDC ligand).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	[Cu(C₈H₄O₅)(C₁₂H₁₀N₄)]
M_r	453.89
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	9.948 (8), 9.955 (7), 12.043 (9)
α, β, γ (°)	66.38 (3), 82.99 (4), 61.08 (2)
V (Å³)	952.6 (12)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.19
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001 )
T_min, T_max	0.853, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	10124, 4299, 3126
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.130, 1.04
No. of reflections	4299
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.69
Computer programs: SMART and SAINT-Plus (Bruker, 2007 ), SHELXL2014 (Sheldrick, 2015 ), SHELXTL (Sheldrick, 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1515776

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2414314616018022/lh4014sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018022/lh4014Isup2.hkl

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Poly[(µ₃-5-hydroxyisophthalato)[µ₂-1,1'-(1,4-phenylene)bis(1H-imidazole)]copper] top

Crystal data top

[Cu(C₈H₄O₅)(C₁₂H₁₀N₄)]	Z = 2
M_r = 453.89	F(000) = 462
Triclinic, P1	D_x = 1.582 Mg m⁻³
a = 9.948 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.955 (7) Å	Cell parameters from 2197 reflections
c = 12.043 (9) Å	θ = 2.3–27.5°
α = 66.38 (3)°	µ = 1.19 mm⁻¹
β = 82.99 (4)°	T = 296 K
γ = 61.08 (2)°	Block, blue
V = 952.6 (12) Å³	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3126 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	R_int = 0.071
φ and ω scans	θ_max = 27.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→12
T_min = 0.853, T_max = 1	k = −12→12
10124 measured reflections	l = −15→15
4299 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0495P)² + 0.2061P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4299 reflections	Δρ_max = 0.46 e Å⁻³
272 parameters	Δρ_min = −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.

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

	x	y	z	U_iso*/U_eq
Cu1	0.66754 (5)	0.97776 (6)	0.39574 (4)	0.02984 (16)
O3	−0.1299 (3)	0.9861 (3)	0.3440 (2)	0.0344 (6)
O1	0.5542 (3)	0.8764 (3)	0.3623 (2)	0.0354 (6)
O2	0.3725 (3)	0.8802 (3)	0.4950 (2)	0.0392 (7)
O4	−0.1334 (3)	0.9181 (3)	0.1879 (2)	0.0406 (7)
O5	0.3567 (3)	0.9019 (4)	−0.0074 (2)	0.0511 (8)
H5	0.2856	0.9594	−0.0613	0.077*
N4	1.5339 (3)	0.1951 (4)	1.2624 (3)	0.0312 (7)
N3	1.3643 (3)	0.3795 (4)	1.1009 (3)	0.0291 (7)
N2	0.9579 (3)	0.6014 (4)	0.7009 (3)	0.0321 (7)
N1	0.7931 (3)	0.7678 (4)	0.5370 (3)	0.0355 (8)
C18	1.4343 (4)	0.2190 (4)	1.1838 (3)	0.0280 (8)
H18	1.4147	0.1361	1.1851	0.034*
C2	0.3368 (4)	0.8714 (4)	0.3064 (3)	0.0247 (7)
C8	−0.0688 (4)	0.9388 (4)	0.2585 (3)	0.0266 (8)
C3	0.3912 (4)	0.8762 (4)	0.1931 (3)	0.0299 (8)
H3	0.4888	0.8661	0.1775	0.036*
C4	0.2985 (4)	0.8964 (5)	0.1030 (3)	0.0308 (8)
C15	1.2612 (4)	0.4388 (4)	0.9979 (3)	0.0274 (8)
C1	0.4282 (4)	0.8745 (4)	0.3975 (3)	0.0263 (7)
C6	0.0964 (4)	0.9072 (4)	0.2403 (3)	0.0239 (7)
C7	0.1893 (4)	0.8869 (4)	0.3304 (3)	0.0248 (7)
H7	0.1534	0.8837	0.4059	0.030*
C5	0.1535 (4)	0.9073 (4)	0.1281 (3)	0.0286 (8)
H5A	0.0943	0.9148	0.0697	0.034*
C14	1.2764 (4)	0.3285 (5)	0.9494 (3)	0.0347 (9)
H14	1.3533	0.2179	0.9830	0.042*
C9	0.8926 (4)	0.7547 (5)	0.6102 (3)	0.0352 (9)
H9	0.9143	0.8397	0.6002	0.042*
C12	1.0637 (4)	0.5460 (4)	0.8018 (3)	0.0304 (8)
C19	1.5278 (4)	0.3485 (5)	1.2289 (3)	0.0404 (10)
H19	1.5854	0.3699	1.2684	0.048*
C13	1.1777 (4)	0.3812 (5)	0.8507 (3)	0.0381 (9)
H13	1.1882	0.3065	0.8182	0.046*
C20	1.4249 (5)	0.4632 (5)	1.1296 (3)	0.0394 (9)
H20	1.4001	0.5749	1.0890	0.047*
C16	1.1469 (5)	0.6036 (5)	0.9492 (3)	0.0412 (10)
H16	1.1364	0.6780	0.9820	0.049*
C17	1.0476 (5)	0.6568 (5)	0.8506 (4)	0.0417 (10)
H17	0.9703	0.7672	0.8176	0.050*
C10	0.8973 (5)	0.5107 (5)	0.6846 (4)	0.0459 (11)
H10	0.9208	0.4008	0.7328	0.055*
C11	0.7964 (5)	0.6151 (5)	0.5838 (4)	0.0443 (10)
H11	0.7380	0.5877	0.5509	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0259 (2)	0.0386 (3)	0.0216 (2)	−0.0161 (2)	−0.00973 (17)	−0.00445 (18)
O3	0.0231 (13)	0.0513 (16)	0.0316 (14)	−0.0191 (12)	0.0030 (11)	−0.0176 (12)
O1	0.0285 (14)	0.0472 (16)	0.0326 (14)	−0.0191 (13)	−0.0073 (11)	−0.0136 (12)
O2	0.0402 (15)	0.0571 (17)	0.0255 (14)	−0.0213 (14)	−0.0022 (12)	−0.0219 (12)
O4	0.0300 (14)	0.0565 (18)	0.0461 (17)	−0.0231 (14)	−0.0032 (12)	−0.0252 (14)
O5	0.0291 (15)	0.095 (2)	0.0294 (15)	−0.0217 (16)	0.0039 (12)	−0.0355 (16)
N4	0.0270 (16)	0.0384 (18)	0.0226 (15)	−0.0132 (14)	−0.0073 (12)	−0.0074 (13)
N3	0.0300 (16)	0.0303 (16)	0.0223 (15)	−0.0115 (14)	−0.0065 (12)	−0.0072 (12)
N2	0.0293 (16)	0.0287 (16)	0.0274 (16)	−0.0092 (14)	−0.0139 (13)	−0.0021 (13)
N1	0.0304 (17)	0.0398 (19)	0.0303 (17)	−0.0169 (15)	−0.0143 (13)	−0.0035 (14)
C18	0.0252 (18)	0.035 (2)	0.0220 (18)	−0.0112 (16)	−0.0049 (14)	−0.0120 (15)
C2	0.0236 (17)	0.0282 (18)	0.0225 (17)	−0.0115 (15)	−0.0050 (14)	−0.0093 (14)
C8	0.0243 (18)	0.0269 (18)	0.0274 (19)	−0.0137 (15)	−0.0050 (14)	−0.0056 (14)
C3	0.0180 (17)	0.042 (2)	0.0304 (19)	−0.0116 (16)	−0.0005 (14)	−0.0181 (16)
C4	0.0252 (18)	0.042 (2)	0.0240 (18)	−0.0108 (17)	−0.0002 (14)	−0.0172 (16)
C15	0.0213 (17)	0.0310 (19)	0.0203 (17)	−0.0071 (15)	−0.0061 (13)	−0.0060 (14)
C1	0.0257 (18)	0.0239 (17)	0.0240 (18)	−0.0099 (15)	−0.0092 (14)	−0.0039 (14)
C6	0.0211 (17)	0.0271 (18)	0.0243 (17)	−0.0121 (15)	−0.0028 (13)	−0.0087 (14)
C7	0.0254 (18)	0.0315 (18)	0.0203 (17)	−0.0137 (16)	0.0002 (13)	−0.0123 (14)
C5	0.0213 (17)	0.038 (2)	0.0278 (18)	−0.0105 (16)	−0.0061 (14)	−0.0167 (15)
C14	0.0271 (19)	0.032 (2)	0.0278 (19)	0.0009 (16)	−0.0112 (15)	−0.0108 (15)
C9	0.033 (2)	0.035 (2)	0.032 (2)	−0.0160 (18)	−0.0146 (16)	−0.0040 (16)
C12	0.0252 (18)	0.0308 (19)	0.0250 (19)	−0.0078 (16)	−0.0100 (14)	−0.0052 (15)
C19	0.045 (2)	0.050 (2)	0.031 (2)	−0.027 (2)	−0.0122 (17)	−0.0094 (18)
C13	0.038 (2)	0.036 (2)	0.032 (2)	−0.0065 (18)	−0.0131 (17)	−0.0140 (17)
C20	0.050 (2)	0.034 (2)	0.035 (2)	−0.022 (2)	−0.0095 (18)	−0.0083 (17)
C16	0.046 (2)	0.032 (2)	0.039 (2)	−0.0102 (19)	−0.0174 (18)	−0.0114 (17)
C17	0.046 (2)	0.0236 (19)	0.042 (2)	−0.0079 (18)	−0.0210 (19)	−0.0053 (17)
C10	0.054 (3)	0.034 (2)	0.044 (2)	−0.023 (2)	−0.019 (2)	−0.0016 (18)
C11	0.048 (3)	0.038 (2)	0.046 (2)	−0.023 (2)	−0.022 (2)	−0.0053 (18)

Geometric parameters (Å, º) top

Cu1—N1	1.992 (3)	C2—C1	1.527 (4)
Cu1—N4ⁱ	1.995 (3)	C8—C6	1.521 (5)
Cu1—O1	1.997 (3)	C3—C4	1.399 (5)
Cu1—O3ⁱⁱ	2.066 (3)	C3—H3	0.9300
Cu1—O2ⁱⁱⁱ	2.170 (3)	C4—C5	1.397 (5)
O3—C8	1.269 (4)	C15—C14	1.379 (5)
O3—Cu1^iv	2.066 (3)	C15—C16	1.384 (5)
O1—C1	1.280 (4)	C6—C7	1.400 (4)
O2—C1	1.246 (4)	C6—C5	1.399 (5)
O2—Cu1ⁱⁱⁱ	2.170 (3)	C7—H7	0.9300
O4—C8	1.257 (4)	C5—H5A	0.9300
O5—C4	1.376 (4)	C14—C13	1.393 (5)
O5—H5	0.8200	C14—H14	0.9300
N4—C18	1.324 (4)	C9—H9	0.9300
N4—C19	1.387 (5)	C12—C13	1.384 (5)
N4—Cu1^v	1.995 (3)	C12—C17	1.384 (5)
N3—C18	1.360 (4)	C19—C20	1.363 (5)
N3—C20	1.394 (5)	C19—H19	0.9300
N3—C15	1.441 (4)	C13—H13	0.9300
N2—C9	1.351 (5)	C20—H20	0.9300
N2—C10	1.384 (5)	C16—C17	1.393 (5)
N2—C12	1.449 (4)	C16—H16	0.9300
N1—C9	1.331 (4)	C17—H17	0.9300
N1—C11	1.378 (5)	C10—C11	1.356 (5)
C18—H18	0.9300	C10—H10	0.9300
C2—C3	1.397 (5)	C11—H11	0.9300
C2—C7	1.405 (5)

N1—Cu1—N4ⁱ	176.06 (13)	C16—C15—N3	120.6 (3)
N1—Cu1—O1	91.42 (13)	O2—C1—O1	126.8 (3)
N4ⁱ—Cu1—O1	89.73 (13)	O2—C1—C2	118.2 (3)
N1—Cu1—O3ⁱⁱ	87.23 (13)	O1—C1—C2	115.0 (3)
N4ⁱ—Cu1—O3ⁱⁱ	94.62 (12)	C7—C6—C5	119.4 (3)
O1—Cu1—O3ⁱⁱ	134.81 (11)	C7—C6—C8	121.6 (3)
N1—Cu1—O2ⁱⁱⁱ	89.72 (13)	C5—C6—C8	118.9 (3)
N4ⁱ—Cu1—O2ⁱⁱⁱ	86.76 (13)	C6—C7—C2	119.9 (3)
O1—Cu1—O2ⁱⁱⁱ	133.92 (11)	C6—C7—H7	120.1
O3ⁱⁱ—Cu1—O2ⁱⁱⁱ	91.26 (11)	C2—C7—H7	120.1
C8—O3—Cu1^iv	116.7 (2)	C4—C5—C6	120.7 (3)
C1—O1—Cu1	132.2 (2)	C4—C5—H5A	119.6
C1—O2—Cu1ⁱⁱⁱ	137.8 (2)	C6—C5—H5A	119.6
C4—O5—H5	109.5	C15—C14—C13	120.6 (3)
C18—N4—C19	105.6 (3)	C15—C14—H14	119.7
C18—N4—Cu1^v	125.6 (3)	C13—C14—H14	119.7
C19—N4—Cu1^v	128.7 (2)	N1—C9—N2	110.8 (3)
C18—N3—C20	106.4 (3)	N1—C9—H9	124.6
C18—N3—C15	124.3 (3)	N2—C9—H9	124.6
C20—N3—C15	128.9 (3)	C13—C12—C17	120.4 (3)
C9—N2—C10	107.5 (3)	C13—C12—N2	119.6 (3)
C9—N2—C12	126.1 (3)	C17—C12—N2	120.0 (3)
C10—N2—C12	126.2 (3)	C20—C19—N4	109.8 (3)
C9—N1—C11	105.7 (3)	C20—C19—H19	125.1
C9—N1—Cu1	122.9 (3)	N4—C19—H19	125.1
C11—N1—Cu1	131.3 (2)	C12—C13—C14	119.1 (3)
N4—C18—N3	111.9 (3)	C12—C13—H13	120.4
N4—C18—H18	124.1	C14—C13—H13	120.4
N3—C18—H18	124.1	C19—C20—N3	106.3 (3)
C3—C2—C7	120.3 (3)	C19—C20—H20	126.9
C3—C2—C1	119.5 (3)	N3—C20—H20	126.9
C7—C2—C1	119.6 (3)	C15—C16—C17	119.3 (4)
O4—C8—O3	125.7 (3)	C15—C16—H16	120.4
O4—C8—C6	118.0 (3)	C17—C16—H16	120.4
O3—C8—C6	116.3 (3)	C12—C17—C16	120.3 (3)
C2—C3—C4	119.9 (3)	C12—C17—H17	119.9
C2—C3—H3	120.1	C16—C17—H17	119.9
C4—C3—H3	120.1	C11—C10—N2	105.8 (3)
O5—C4—C5	122.6 (3)	C11—C10—H10	127.1
O5—C4—C3	117.7 (3)	N2—C10—H10	127.1
C5—C4—C3	119.7 (3)	C10—C11—N1	110.2 (3)
C14—C15—C16	120.3 (3)	C10—C11—H11	124.9
C14—C15—N3	119.1 (3)	N1—C11—H11	124.9

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4^vi	0.82	1.84	2.660 (4)	177

Symmetry code: (vi) −x, −y+2, −z.

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