catena-Poly[[bis­(pyridine-κN)zinc]-μ-5-carb­oxy­benzene-1,3-di­carboxyl­ato-κ2O1:O3]

Yotnoi, B.; Rujiwatra, A.

doi:10.1107/S1600536813014347

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page m345

doi:10.1107/S1600536813014347

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catena-Poly[[bis(pyridine-κN)zinc]-μ-5-carboxybenzene-1,3-dicarboxylato-κ²O¹:O³]

Bunlawee Yotnoi ^a and Apinpus Rujiwatra ^b ^*

^aDivision of Chemistry, School of Science, University of Phayao, Phayao 56000, Thailand, and ^bDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
^*Correspondence e-mail: apinpus@chiangmai.ac.th

(Received 14 May 2013; accepted 23 May 2013; online 31 May 2013)

The title one-dimensional coordination polymer, [Zn(C₉H₄O₆)(C₅H₅N)₂]_n or [Zn(HBTC)(py)₂]_n, (I), where BTC is benzene-1,3,5-tricarboxylate and py is pyridine, is a solvent-free polymorph of [Zn(HBTC)(py)₂]·2C₂H₅OH [Yaghi et al. (1997 ). Chem. Mater. 9, 1074–1076]. Differences in the spatial arrangements and supramolecular packing of the [Zn(HBTC)(py)₂]_n chains in the two structures are described. The chain in (I) extends parallel to [100] and is severely puckered, with a Zn⋯Zn distance of 8.3599 (3) Å and a Zn⋯Zn⋯Zn angle of 107.516 (3)°, as a result of hydrogen-bonding interactions of the types O—H⋯O and C—H⋯O. There is no evidence for π–π interactions in (I). The differences between the solvent-free and solvent-containing structures can be accounted for by the absence of the ethanol solvent molecule and the use of the converging pair of O atoms in the bis-monodentate bridging HBTC²⁻ ligand in (I).

Related literature

For the ethanol monosolvate of (I), see: Yaghi et al. (1997). For a review on supramolecular isomerism in coordination compounds, see: Zhang et al. (2009 ).

Experimental

Crystal data

[Zn(C₉H₄O₆)(C₅H₅N)₂]
M_r = 431.69
Orthorhombic, P b c a
a = 13.4850 (4) Å
b = 15.7677 (4) Å
c = 16.7252 (4) Å
V = 3556.24 (16) Å³
Z = 8
Mo Kα radiation
μ = 1.42 mm⁻¹
T = 293 K
0.40 × 0.32 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.638, T_max = 0.746
18851 measured reflections
4402 independent reflections
3448 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.075
S = 1.03
4402 reflections
257 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5W⋯O3ⁱ	0.86 (3)	1.74 (3)	2.5813 (19)	164 (3)
C1—H1⋯O1	0.93	2.45	3.053 (2)	122
C5—H5⋯O6ⁱⁱ	0.93	2.39	3.129 (3)	136
C17—H17⋯O5	0.93	2.37	2.693 (2)	100
C17—H17⋯O5ⁱ	0.93	2.42	3.309 (2)	159
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ) and WinGX (Farrugia, 2012 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008) and WinGX; molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813014347/cq2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813014347/cq2004Isup2.hkl

checkCIF report

Comment top

The reported complex [Zn(HBTC)(py)₂]_n (I), where BTC = 1,3,5-benzenetricarboxylate and pyr = pyridine (C₅H₅N), is a supramolecular isomer of the previously reported [Zn(HBTC)(py)₂].2C₂H₅OH (Yaghi et al., 1997). It is clear that the two isomers result from differences in the synthesis method. In order to synthesize I, a simple solution route was adopted, whereas the crystals of [Zn(HBTC)(py)₂].2C₂H₅OH have only been synthesized when poly(ethyleneoxide) (PEO) gel is used as the reaction medium in the presence of C₂H₅OH as solvent (Yaghi et al., 1997). The absence or presence of the C₂H₅OH solvent molecules results in different spatial arrangements and supramolecular packing in the two isomers.

While the two supramolecular isomers are built up of the same structural building motifs, i.e. a tetrahedral Zn(II) ion, two monodentate pyr molecules and a bridging HBTC^2- anion, the architecture of the one-dimensional chains of the two isomers notably differs. In the case of I, an asymmetric unit comprises a tetrahedral Zn(II) ion (Fig. 1), coordinated by two N atoms (N1 and N2) from two crystallographically independent pyr molecules and two O atoms (O1 and O2) from two distinct carboxylato groups of the HBTC^2- anion. The HBTC^2- ligand in structure I adopts a bis-monodentate bridging mode (µ₂-η¹:η¹:η⁰:η⁰:η⁰:η⁰) (Fig. 2), linking two adjacent Zn(II) ions to form a one-dimensional chain of chemical composition [Zn(HBTC)(py)₂]_n, extending in the [1 0 0] direction. Because of the converging positions of the coordinating O1 and O2 atoms, the derived chain is severely puckered with a Zn···Zn distance of 8.3599 (3) Å and a Zn···Zn···Zn angle of 107.516 (3)°. In comparison, the one-dimensional chain of the previously reported [Zn(HBTC)(py)₂].2C₂H₅OH isomer is almost linear with corresponding distance and angle values of 10.162 (2) Å and 180°, respectively. The presence of the C₂H₅OH solvent molecule in the vicinity of the two coordinating carboxylato groups in the [Zn(HBTC)(py)₂].2C₂H₅OH isomer ostensibly forces the coordinating atoms to be the diverging pair of O atoms (equivalent to O3 and O6 in I), rather than the converging pair as in I.

A larger degree of puckering in I compared to that of the previously reported isomer imparts an immense influence on the corresponding supramolecular interactions and packing. While there are no π–π interactions in I, which is in contrast to the [Zn(HBTC)(py)₂].2C₂H₅OH case, an acidic proton of the bridging HBTC^2- anion is involved in the hydrogen bonding interactions with the O atom of the HBTC^2- anion from the adjacent chain (Fig. 3). Weak C—H···O hydrogen bonding interactions further link these one-dimensional chains into a dense, three-dimensional supramolecular structure.

Related literature top

For the supramolecular isomer structure, Zn(HBTC)(NC₅H₅)₂.C₂H₅OH, see: Yaghi et al. (1997). For a review on supramolecular isomerism in coordination compounds, see: Zhang et al. (2009).

Experimental top

A small fraction of pyridine (0.50 ml, 6.18 mmol; 99.8% Sigma-Aldrich) was gradually added to a 2.50 ml of a 0.204 molL^-1 aqueous solution of 1,3,5-benzenetricarboxylic acid (H₃BTC; 0.509 mmol; 95% Sigma-Aldrich) with stirring until the acid was completely dissolved. Then 2.50 ml of 0.296 molL^-1 ZnSO₄.7H₂O (aq) solution (0.741 mmol; 99% Sigma-Aldrich) was added, giving a clear solution. The solution was left at ambient temperature for 2 days before the colourless crystals of I started to crystallize.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and WinGX (Farrugia, 2012); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008) and WinGX (Farrugia, 2012); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of an extended unit of I with atom numbering scheme. Displacement ellipsoids are drawn at the 70% probability level. [Symmetry codes: (i) 1/2 + x, 0.5 - y, 1 - z; (ii) -1/2 + x, 0.5 - y, 1 - z]
	Fig. 2. View of the one-dimensional chain of I. Hydrogen atoms are omitted for clarity.
	Fig. 3. View of supramolecular packing in I, directed primarily by the O—H···O hydrogen bonding interactions (dotted lines).

catena-Poly[[bis(pyridine-κN)zinc]-µ-5-carboxybenzene-1,3-dicarboxylato-κ²O¹:O³] top

Crystal data top

[Zn(C₉H₄O₆)(C₅H₅N)₂]	D_x = 1.613 Mg m⁻³
M_r = 431.69	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 12396 reflections
a = 13.4850 (4) Å	θ = 2.3–28.3°
b = 15.7677 (4) Å	µ = 1.42 mm⁻¹
c = 16.7252 (4) Å	T = 293 K
V = 3556.24 (16) Å³	Block, colorless
Z = 8	0.40 × 0.32 × 0.20 mm
F(000) = 1760

Data collection top

Bruker SMART CCD area-detector diffractometer	3448 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
ω scan	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→16
T_min = 0.638, T_max = 0.746	k = −18→21
18851 measured reflections	l = −22→18
4402 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0343P)² + 1.2882P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4402 reflections	Δρ_max = 0.32 e Å⁻³
257 parameters	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Zn(C₉H₄O₆)(C₅H₅N)₂]	V = 3556.24 (16) Å³
M_r = 431.69	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.4850 (4) Å	µ = 1.42 mm⁻¹
b = 15.7677 (4) Å	T = 293 K
c = 16.7252 (4) Å	0.40 × 0.32 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4402 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3448 reflections with I > 2σ(I)
T_min = 0.638, T_max = 0.746	R_int = 0.027
18851 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.32 e Å⁻³
4402 reflections	Δρ_min = −0.27 e Å⁻³
257 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Zn1	0.13687 (2)	0.15689 (2)	0.38115 (2)	0.02934 (7)
O1	0.22574 (9)	0.24099 (8)	0.43444 (8)	0.0387 (3)
O2	0.02076 (9)	0.12804 (8)	0.44224 (8)	0.0380 (3)
O3	0.08532 (9)	0.31056 (8)	0.42911 (9)	0.0403 (3)
O4	0.17223 (13)	0.64303 (10)	0.62643 (11)	0.0636 (5)
O5	0.06430 (11)	0.59328 (10)	0.53854 (11)	0.0610 (5)
O6	0.50499 (11)	0.48839 (11)	0.63064 (10)	0.0572 (4)
N1	0.24456 (11)	0.07341 (9)	0.34795 (9)	0.0344 (3)
N2	0.08742 (12)	0.20600 (9)	0.27386 (9)	0.0351 (3)
C1	0.34018 (14)	0.09488 (13)	0.35799 (13)	0.0403 (4)
H1	0.3551	0.1456	0.3837	0.048*
C2	0.41665 (16)	0.04472 (14)	0.33178 (15)	0.0526 (6)
H2	0.4821	0.0612	0.3398	0.063*
C3	0.39544 (18)	−0.02992 (14)	0.29374 (14)	0.0554 (6)
H3	0.4463	−0.0645	0.2749	0.066*
C4	0.29877 (19)	−0.05299 (13)	0.28377 (14)	0.0554 (6)
H4	0.2829	−0.1038	0.2586	0.066*
C5	0.22515 (16)	−0.00031 (13)	0.31132 (12)	0.0451 (5)
H5	0.1594	−0.0164	0.3043	0.054*
C6	0.14604 (16)	0.21440 (13)	0.21013 (12)	0.0455 (5)
H6	0.2091	0.1906	0.2119	0.055*
C7	0.1175 (2)	0.25651 (16)	0.14217 (13)	0.0581 (6)
H7	0.1607	0.2614	0.0991	0.070*
C8	0.0245 (2)	0.29120 (16)	0.13863 (15)	0.0639 (7)
H8	0.0034	0.3200	0.0932	0.077*
C9	−0.03721 (19)	0.28258 (14)	0.20360 (15)	0.0570 (6)
H9	−0.1010	0.3050	0.2025	0.068*
C10	−0.00334 (15)	0.24024 (12)	0.27043 (12)	0.0424 (5)
H10	−0.0449	0.2353	0.3145	0.051*
C11	0.17367 (13)	0.30629 (11)	0.44909 (10)	0.0290 (3)
C12	0.22248 (12)	0.37837 (10)	0.49276 (10)	0.0274 (3)
C13	0.32159 (13)	0.37427 (11)	0.51554 (10)	0.0290 (4)
H13	0.3589	0.3265	0.5029	0.035*
C14	0.36539 (12)	0.44093 (11)	0.55706 (10)	0.0296 (4)
C15	0.30929 (13)	0.51149 (11)	0.57672 (11)	0.0325 (4)
H15	0.3381	0.5560	0.6048	0.039*
C16	0.20993 (12)	0.51606 (11)	0.55457 (11)	0.0311 (4)
C17	0.16744 (13)	0.44966 (11)	0.51237 (11)	0.0306 (4)
H17	0.1013	0.4530	0.4970	0.037*
C18	0.14864 (13)	0.59105 (12)	0.57802 (13)	0.0377 (4)
C19	0.47177 (13)	0.43569 (11)	0.58439 (11)	0.0322 (4)
H5W	0.022 (2)	0.6310 (19)	0.5540 (18)	0.096 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02247 (11)	0.02948 (11)	0.03608 (12)	−0.00104 (8)	0.00170 (8)	−0.00546 (8)
O1	0.0273 (7)	0.0301 (6)	0.0587 (8)	0.0041 (5)	−0.0047 (6)	−0.0160 (6)
O2	0.0269 (7)	0.0399 (7)	0.0472 (7)	−0.0100 (5)	0.0077 (6)	−0.0080 (6)
O3	0.0262 (7)	0.0345 (7)	0.0604 (9)	0.0031 (5)	−0.0077 (6)	−0.0175 (6)
O4	0.0489 (9)	0.0533 (10)	0.0887 (13)	0.0178 (8)	−0.0231 (9)	−0.0421 (9)
O5	0.0303 (8)	0.0560 (10)	0.0967 (13)	0.0175 (7)	−0.0177 (8)	−0.0409 (9)
O6	0.0325 (8)	0.0634 (10)	0.0759 (11)	0.0070 (7)	−0.0159 (7)	−0.0354 (8)
N1	0.0317 (8)	0.0309 (8)	0.0407 (8)	0.0036 (6)	0.0055 (7)	−0.0024 (7)
N2	0.0352 (9)	0.0350 (8)	0.0352 (8)	0.0005 (7)	−0.0019 (7)	−0.0053 (7)
C1	0.0338 (10)	0.0344 (10)	0.0526 (11)	0.0012 (8)	0.0058 (9)	−0.0005 (9)
C2	0.0342 (11)	0.0496 (12)	0.0740 (16)	0.0100 (9)	0.0150 (10)	0.0077 (11)
C3	0.0593 (15)	0.0445 (12)	0.0625 (14)	0.0220 (11)	0.0265 (12)	0.0054 (11)
C4	0.0711 (16)	0.0364 (11)	0.0587 (14)	0.0090 (11)	0.0144 (12)	−0.0115 (10)
C5	0.0442 (12)	0.0368 (10)	0.0544 (12)	0.0002 (9)	0.0051 (10)	−0.0112 (9)
C6	0.0488 (13)	0.0469 (11)	0.0408 (11)	−0.0019 (10)	0.0059 (9)	−0.0068 (9)
C7	0.0817 (18)	0.0554 (14)	0.0373 (11)	−0.0166 (13)	0.0046 (11)	−0.0009 (11)
C8	0.094 (2)	0.0476 (13)	0.0500 (14)	−0.0149 (14)	−0.0259 (14)	0.0094 (11)
C9	0.0558 (15)	0.0443 (12)	0.0710 (16)	0.0029 (11)	−0.0223 (12)	0.0006 (11)
C10	0.0403 (11)	0.0397 (10)	0.0472 (11)	0.0016 (9)	−0.0036 (9)	−0.0043 (9)
C11	0.0273 (8)	0.0256 (8)	0.0342 (9)	−0.0003 (7)	0.0012 (7)	−0.0049 (7)
C12	0.0239 (8)	0.0256 (8)	0.0328 (8)	−0.0012 (6)	0.0005 (7)	−0.0037 (7)
C13	0.0239 (8)	0.0272 (8)	0.0358 (9)	0.0041 (7)	0.0006 (7)	−0.0042 (7)
C14	0.0224 (8)	0.0321 (9)	0.0342 (9)	0.0018 (7)	−0.0015 (7)	−0.0028 (7)
C15	0.0258 (9)	0.0304 (9)	0.0414 (10)	−0.0007 (7)	−0.0038 (7)	−0.0100 (8)
C16	0.0242 (8)	0.0287 (8)	0.0404 (9)	0.0023 (7)	−0.0015 (7)	−0.0080 (7)
C17	0.0215 (8)	0.0300 (9)	0.0404 (10)	0.0008 (7)	−0.0027 (7)	−0.0057 (7)
C18	0.0256 (9)	0.0338 (9)	0.0536 (12)	0.0040 (7)	−0.0019 (8)	−0.0114 (9)
C19	0.0246 (8)	0.0359 (9)	0.0361 (9)	0.0021 (7)	−0.0013 (7)	−0.0018 (8)

Geometric parameters (Å, º) top

Zn1—O2	1.9241 (12)	C5—H5	0.9300
Zn1—O1	1.9973 (12)	C6—C7	1.371 (3)
Zn1—N1	2.0371 (14)	C6—H6	0.9300
Zn1—N2	2.0650 (15)	C7—C8	1.370 (4)
O1—C11	1.270 (2)	C7—H7	0.9300
O2—C19ⁱ	1.283 (2)	C8—C9	1.375 (4)
O3—C11	1.239 (2)	C8—H8	0.9300
O4—C18	1.195 (2)	C9—C10	1.380 (3)
O5—C18	1.315 (2)	C9—H9	0.9300
O5—H5W	0.86 (3)	C10—H10	0.9300
O6—C19	1.220 (2)	C11—C12	1.503 (2)
N1—C5	1.340 (2)	C12—C17	1.386 (2)
N1—C1	1.344 (2)	C12—C13	1.391 (2)
N2—C6	1.334 (3)	C13—C14	1.391 (2)
N2—C10	1.339 (2)	C13—H13	0.9300
C1—C2	1.372 (3)	C14—C15	1.385 (2)
C1—H1	0.9300	C14—C19	1.508 (2)
C2—C3	1.368 (3)	C15—C16	1.392 (2)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.364 (3)	C16—C17	1.387 (2)
C3—H3	0.9300	C16—C18	1.495 (2)
C4—C5	1.374 (3)	C17—H17	0.9300
C4—H4	0.9300	C19—O2ⁱⁱ	1.283 (2)

O2—Zn1—O1	114.10 (5)	C7—C8—C9	118.7 (2)
O2—Zn1—N1	124.90 (6)	C7—C8—H8	120.6
O1—Zn1—N1	97.06 (6)	C9—C8—H8	120.6
O2—Zn1—N2	106.70 (6)	C8—C9—C10	119.2 (2)
O1—Zn1—N2	109.43 (6)	C8—C9—H9	120.4
N1—Zn1—N2	103.63 (6)	C10—C9—H9	120.4
C11—O1—Zn1	107.01 (11)	N2—C10—C9	122.2 (2)
C19ⁱ—O2—Zn1	114.84 (11)	N2—C10—H10	118.9
C18—O5—H5W	116 (2)	C9—C10—H10	118.9
C5—N1—C1	117.60 (17)	O3—C11—O1	121.57 (15)
C5—N1—Zn1	123.09 (13)	O3—C11—C12	120.73 (15)
C1—N1—Zn1	119.16 (13)	O1—C11—C12	117.69 (15)
C6—N2—C10	117.87 (18)	C17—C12—C13	119.16 (15)
C6—N2—Zn1	122.71 (14)	C17—C12—C11	119.58 (15)
C10—N2—Zn1	118.92 (13)	C13—C12—C11	121.25 (15)
N1—C1—C2	122.4 (2)	C12—C13—C14	120.63 (15)
N1—C1—H1	118.8	C12—C13—H13	119.7
C2—C1—H1	118.8	C14—C13—H13	119.7
C3—C2—C1	119.2 (2)	C15—C14—C13	119.57 (15)
C3—C2—H2	120.4	C15—C14—C19	119.45 (15)
C1—C2—H2	120.4	C13—C14—C19	120.92 (15)
C4—C3—C2	119.09 (19)	C14—C15—C16	120.28 (16)
C4—C3—H3	120.5	C14—C15—H15	119.9
C2—C3—H3	120.5	C16—C15—H15	119.9
C3—C4—C5	119.2 (2)	C17—C16—C15	119.61 (15)
C3—C4—H4	120.4	C17—C16—C18	120.15 (15)
C5—C4—H4	120.4	C15—C16—C18	120.22 (15)
N1—C5—C4	122.5 (2)	C12—C17—C16	120.75 (16)
N1—C5—H5	118.8	C12—C17—H17	119.6
C4—C5—H5	118.8	C16—C17—H17	119.6
N2—C6—C7	123.0 (2)	O4—C18—O5	123.49 (18)
N2—C6—H6	118.5	O4—C18—C16	124.95 (17)
C7—C6—H6	118.5	O5—C18—C16	111.55 (16)
C8—C7—C6	119.1 (2)	O6—C19—O2ⁱⁱ	124.36 (17)
C8—C7—H7	120.5	O6—C19—C14	120.27 (16)
C6—C7—H7	120.5	O2ⁱⁱ—C19—C14	115.32 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5W···O3ⁱⁱⁱ	0.86 (3)	1.74 (3)	2.5813 (19)	164 (3)
C1—H1···O1	0.93	2.45	3.053 (2)	122
C5—H5···O6ⁱ	0.93	2.39	3.129 (3)	136
C17—H17···O5	0.93	2.37	2.693 (2)	100
C17—H17···O5ⁱⁱⁱ	0.93	2.42	3.309 (2)	159

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

Experimental details

Crystal data
Chemical formula	[Zn(C₉H₄O₆)(C₅H₅N)₂]
M_r	431.69
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	13.4850 (4), 15.7677 (4), 16.7252 (4)
V (Å³)	3556.24 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.42
Crystal size (mm)	0.40 × 0.32 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.638, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	18851, 4402, 3448
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.03
No. of reflections	4402
No. of parameters	257
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008) and WinGX (Farrugia, 2012), SHELXL2013 (Sheldrick, 2008) and WinGX (Farrugia, 2012), DIAMOND (Brandenburg, 1999), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5W···O3ⁱ	0.86 (3)	1.74 (3)	2.5813 (19)	164 (3)
C1—H1···O1	0.93	2.45	3.053 (2)	122.2
C5—H5···O6ⁱⁱ	0.93	2.39	3.129 (3)	136.2
C17—H17···O5	0.93	2.37	2.693 (2)	100.0
C17—H17···O5ⁱ	0.93	2.42	3.309 (2)	159.2

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

Acknowledgements

This work was financially supported by the Thailand Research Fund and the National Research University Project.

References

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