catena-Poly[[[[bis(pyridin-2-yl-κN)amine]zinc(II)]-μ2-(2E,4E)-hexa-2,4-dienedioato-κ4O1,O1′:O6,O6′] monohydrate]

Lee, D.N.; Kim, Y.

doi:10.1107/S2414314616006362

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160636

doi:10.1107/S2414314616006362

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catena-Poly[[[[bis(pyridin-2-yl-κN)amine]zinc(II)]-μ₂-(2E,4E)-hexa-2,4-dienedioato-κ⁴O¹,O^1′:O⁶,O^6′] monohydrate]

Do Nam Lee ^a and Youngmee Kim ^b ^*

^aDivision of General Education (Chemistry), Kwangwoon University, Seoul 01897, Republic of Korea, and ^bDepartment of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Republic of Korea
^*Correspondence e-mail: ymeekim@ewha.ac.kr

Edited by A. J. Lough, University of Toronto, Canada (Received 1 April 2016; accepted 15 April 2016; online 22 April 2016)

In the title compound, {[Zn(C₆H₄O₄)(C₁₀H₉N₃)]·H₂O}_n, the di(pyridin-2-yl)amine (dpa) ligands chelate the Zn^II ions, forming [Zn(dpa)]²⁺ units which are connected by two independent bridging muconate [(2E,4E)-hexa-2,4-dienedioate] ligands to form chains. A crystallographic inversion centre is located at the mid-point of the central C—C bond of each muconate ligand. The carboxylate groups of the muconate ligands bridge the Zn^II ions in asymmetric chelating modes. The Zn^II ion is coordinated by four O atoms of two chelating carboxylate groups and two pyridyl N atoms in a distorted octahedral coordination environment. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds connect chains and solvent water molecules, forming a two-dimensional network parallel to (101).

Keywords: crystal structure; Zn–MOF; muconate; di(pyridin-2-yl)amine; hydrogen bonds.

CCDC reference: 1474269

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Chemical scheme

Structure description

Metal–organic frameworks (MOFs), constructed from metal ions and polytopic bridging ligands, have been used for selective gas sorption, heterogeneous catalysis, separation, sensors, drug delivery and biological imaging. Dicarboxylates have provided structures of various dimensionalities with different coordination modes and pore sizes. Rigid aromatic dicarboxylates (Sumida et al., 2012 ) have been used for the synthesis of MOFs, and flexible cyclohexanedicarboxylates (Lee et al. 2011 ; Kim et al. 2011 ) have also been used. One particular group of flexible dicarboxylates, α,ω-alkane-dicarboxylates, has been shown to be particularly suitable as ligands in MOFs of various topologies. Though less frequently employed in MOFs than aromatic dicarboxylates, recently a systematic investigation of MOFs containing these α,ω-alkane (or alkene)-dicarboxylate has been reported (Hyun et al. 2013 ; Hwang et al., 2012 , 2013 ; Lee et al. 2014 ). We report herein the crystal structure of the title compound.

A fragment of the one-dimensional title compound, in which 2,2′-dipyridylamine ligands chelate Zn^II ions to form [Zn(C₁₀H₉N₃)]²⁺ units, is shown in Fig. 1. The units are connected by two independent bridging muconate ligands, forming chains along [011] (Fig. 2). The carboxylate groups of the muconate ligands bridge Zn^II ions in asymmetric chelating modes. A crystallographic inversion centre is located at the mid-point of the central C—-C bond of each muconate ligand. The Zn^II ion is coordinated by four O atoms of two chelating carboxyaltes and two pyridyl N atoms in a distorted octahedral coordination environment.

Figure 1
A fragment of the one-dimensional structure of the title compound showing displacement ellipsoids at the 50% probability level [symmetry codes: (i) 1 − x, 1 − y, 1 − z; (ii) 1 − x, −y, −z].

Figure 2
The one-dimensional structure of the title compound. Solvent water molecules are omitted for clarity.

In the crystal, N—H⋯O and O—H⋯O hydrogen bonds (Table 1) connect the chains and solvent water molecules, forming a two-dimensional network parallel to (101) (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N22—H22N⋯O1Wⁱ	0.88	1.97	2.835 (3)	168
O1W—H1WB⋯O12	0.93 (1)	1.88 (1)	2.791 (3)	165 (3)
O1W—H1WA⋯O13ⁱⁱ	0.93 (1)	1.89 (1)	2.816 (3)	172 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 3
Part of the crystal structure showing a hydrogen-bonded layer parallel to (101). Hydrogen bonds are shown as green dotted lines.

Synthesis and crystallization

Muconic acid (0.1 mmol, 14.2 mg) and Zn(NO₃)₂·6H₂O (0.1 mmol, 30.4 mg) were dissolved in 4 ml H₂O and carefully layered with a 4 ml acetonitrile solution of 2,2′-dipyridylaime (0.2 mmol, 34.2 mg). Suitable crystals of the title compound were obtained in a few weeks.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	[Zn(C₆H₄O₄)(C₁₀H₉N₃)]·H₂O
M_r	394.68
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	170
a, b, c (Å)	8.9885 (13), 15.430 (2), 11.4182 (16)
β (°)	91.806 (2)
V (Å³)	1582.8 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.59
Crystal size (mm)	0.20 × 0.08 × 0.08

Data collection
Diffractometer	Bruker APEX CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	8674, 3089, 2391
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.083, 0.91
No. of reflections	3089
No. of parameters	232
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.51
Computer programs: SMART and SAINT (Bruker, 1997 ), SHELXS97 and SHELXTL (Sheldrick, 2008 ) and SHELXL2013 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1474269

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616006362/lh4006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616006362/lh4006Isup2.hkl

checkCIF report

Chemical context top

Metal–organic frameworks (MOFs) have been constructed by metal ions and polytopic bridging ligands, and used for selective gas sorption, heterogeneous catalysis, separation, sensor, drug delivery, and biological imaging. Dicarboxylates have provided structures of various dimensionalities with different coordination modes and pore sizes. Rigid aromatic dicarboxylates (Sumida, et al., 2012) have been used for the synthesis of MOFs, and flexible cyclohexanedicarboxylates (Lee, et al. 2011; Kim, et al. 2011) have also been used. One particular group of flexible dicarboxylates, α,ω-alkane-dicarboxylates, has been shown to be particularly suitable as ligands in MOFs of various topologies. Though less frequently employed in MOFs than aromatic dicarboxylates, recently a systematic investigation of MOFs containing these α,ω-alkane (or alkene)-dicarboxylate has been reported (Hyun, et al. 2013; Hwang, et al., 2012; Hwang, et al. 2013; Lee, et al. 2014). We report herein the crystal structure of the title compound.

A fragment of the one-dimensional title compound is shown in Fig. 1 in which 2,2'-dipyridylaime ligands chelate ZnII ions to form [Zn(C₁₀H₉N₃)]²⁺ units which are connected by two independent bridging muconate ligands to form one-dimensional chains (Fig. 2). The carboxylate groups of the muconate ligands bridge ZnII ions in asymmetric chelating modes. A crystallographic inversion centre is located at the middle of each central C–C bond of the muconate ligands. The ZnII ion is coordinated by four O atoms of two chelating carboxyaltes and two pyridyl N atoms to form a disotorted octahedral coordination environment. In the crystal, N–H···O and O–H···O hydrogen bonds connect one-dimensional chains and solvent water molecules forming a two-dimensional network parallel to (1 0 1) (Fig. 3).

Synthesis and crystallization top

Muconic acid (0.1 mmol, 14.2 mg) and Zn(NO₃)₂·6H₂O (0.1 mmol, 30.4 mg) were dissolved in 4 mL H₂O and carefully layered by 4 mL acetonitrile solution of 2,2'-dipyridylaime (0.2 mmol, 34.2 mg). Suitable crystals of the title compound were obtained in a few weeks.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms bonded to C atoms were placed in calculated positions with C—H distances of 0.95 Å and an N—H distance of 0.88 Å. They were included in the refinement in riding-motion approximation with U_iso(H) = 1.2U_eq(C) and 1.2U_eq(N). The positions of the H atoms of the water solvent molecule were located in a difference Fourier map and refined with O—H distances restrained to 0.930 (2) Å and U_iso(H) = 1.5U_eq(O).

Related literature top

For rigid aromatic dicarboxylate ligands for MOFs, see: Sumida et al. (2012). For flexible cyclohexanedicarboxylate ligands for MOFs, see: Lee et al. (2011); Kim et al. (2011). For flexible α,ω-alkane-dicarboxylate ligands for MOFs, see: Hwang et al. (2012); Hwang, et al. (2013).

Experimental top

Muconic acid (0.1 mmol, 14.2 mg) and Zn(NO₃)₂·6H₂O (0.1 mmol, 30.4 mg) were dissolved in 4 ml H₂O and carefully layered by 4 ml acetonitrile solution of 2,2'-dipyridylaime (0.2 mmol, 34.2 mg). Suitable crystals of the title compound were obtained in a few weeks.

Structure description top

Metal–organic frameworks (MOFs), constructed from metal ions and polytopic bridging ligands, have been used for selective gas sorption, heterogeneous catalysis, separation, sensors, drug delivery and biological imaging. Dicarboxylates have provided structures of various dimensionalities with different coordination modes and pore sizes. Rigid aromatic dicarboxylates (Sumida et al., 2012) have been used for the synthesis of MOFs, and flexible cyclohexanedicarboxylates (Lee et al. 2011; Kim et al. 2011) have also been used. One particular group of flexible dicarboxylates, α,ω-alkane-dicarboxylates, has been shown to be particularly suitable as ligands in MOFs of various topologies. Though less frequently employed in MOFs than aromatic dicarboxylates, recently a systematic investigation of MOFs containing these α,ω-alkane (or alkene)-dicarboxylate has been reported (Hyun et al. 2013; Hwang et al., 2012, 2013; Lee et al. 2014). We report herein the crystal structure of the title compound.

A fragment of the one-dimensional title compound, in which 2,2'-dipyridylaime ligands chelate Zn^II ions to form [Zn(C₁₀H₉N₃)]²⁺ units is shown in Fig. 1. The units are connected by two independent bridging muconate ligands, forming chains along [???] (Fig. 2). The carboxylate groups of the muconate ligands bridge Zn^II ions in asymmetric chelating modes. A crystallographic inversion centre is located at the mid-point of the central C—-C bond of each muconate ligand. The Zn^II ion is coordinated by four O atoms of two chelating carboxyaltes and two pyridyl N atoms in a distorted octahedral coordination environment.

In the crystal, N—H···O and O—H···O hydrogen bonds (Table 1) connect the chains and solvent water molecules, forming a two-dimensional network parallel to (101) (Fig. 3).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A fragment of the one-dimensional structure of the title compound showing displacement ellipsoids at the 50% probability level [symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 - x, -y, -z].
	Fig. 2. The one-dimensional structure of the title compound. Solvent water molecules are omitted for clarity.
	Fig. 3. Part of the crystal structure showing a hydrogen-bonded layer parallel to (101). Hydrogen bonds are shown as green dotted lines.

catena-Poly[[[[bis(pyridin-2-yl-κN)amine]zinc(II)]-µ₂-(2E,4E)-hexa-2,4-dienedioato-κ⁴O¹,O^1':O⁶,O^6'] monohydrate] top

Crystal data top

[Zn(C₆H₄O₄)(C₁₀H₉N₃)]·H₂O	F(000) = 808
M_r = 394.68	D_x = 1.656 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.9885 (13) Å	Cell parameters from 2966 reflections
b = 15.430 (2) Å	θ = 2.2–26.2°
c = 11.4182 (16) Å	µ = 1.59 mm⁻¹
β = 91.806 (2)°	T = 170 K
V = 1582.8 (4) Å³	Rod, colorless
Z = 4	0.20 × 0.08 × 0.08 mm

Data collection top

Bruker APEX CCD diffractometer	R_int = 0.074
φ and ω scans	θ_max = 26.0°, θ_min = 2.2°
8674 measured reflections	h = −11→10
3089 independent reflections	k = −17→19
2391 reflections with I > 2σ(I)	l = −14→14

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0386P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
3089 reflections	Δρ_max = 0.82 e Å⁻³
232 parameters	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Zn(C₆H₄O₄)(C₁₀H₉N₃)]·H₂O	V = 1582.8 (4) Å³
M_r = 394.68	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.9885 (13) Å	µ = 1.59 mm⁻¹
b = 15.430 (2) Å	T = 170 K
c = 11.4182 (16) Å	0.20 × 0.08 × 0.08 mm
β = 91.806 (2)°

Data collection top

Bruker APEX CCD diffractometer	2391 reflections with I > 2σ(I)
8674 measured reflections	R_int = 0.074
3089 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.82 e Å⁻³
3089 reflections	Δρ_min = −0.51 e Å⁻³
232 parameters

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
Zn1	0.23460 (3)	0.17315 (2)	0.36458 (3)	0.01835 (11)
O11	0.4060 (2)	0.23845 (11)	0.43746 (16)	0.0230 (4)
O12	0.2405 (2)	0.34027 (13)	0.39400 (17)	0.0275 (5)
O13	0.3294 (2)	0.08005 (12)	0.25952 (15)	0.0220 (4)
O14	0.3079 (2)	0.20738 (12)	0.17690 (17)	0.0271 (5)
N21	0.0120 (2)	0.19005 (13)	0.34368 (18)	0.0171 (5)
N22	−0.0519 (2)	0.12860 (14)	0.52676 (18)	0.0202 (5)
H22N	−0.1257	0.1249	0.5754	0.024*
N23	0.2028 (2)	0.09561 (14)	0.50930 (18)	0.0186 (5)
C11	0.3651 (3)	0.31814 (17)	0.4334 (2)	0.0203 (6)
C12	0.4757 (3)	0.38258 (17)	0.4777 (2)	0.0210 (6)
H12	0.5701	0.3626	0.5062	0.025*
C13	0.4478 (3)	0.46740 (16)	0.4790 (2)	0.0189 (6)
H13	0.3528	0.4863	0.4505	0.023*
C14	0.4636 (3)	0.01539 (17)	0.0515 (2)	0.0183 (6)
H14	0.4374	−0.0258	0.1092	0.022*
C15	0.4311 (3)	0.09863 (18)	0.0699 (2)	0.0214 (6)
H15	0.4604	0.1398	0.0133	0.026*
C16	0.3517 (3)	0.13086 (18)	0.1738 (2)	0.0190 (6)
C21	−0.0364 (3)	0.22925 (18)	0.2433 (2)	0.0227 (6)
H21	0.0344	0.2430	0.1862	0.027*
C22	−0.1815 (3)	0.24981 (18)	0.2204 (3)	0.0278 (7)
H22	−0.2112	0.2756	0.1478	0.033*
C23	−0.2856 (3)	0.23254 (18)	0.3048 (2)	0.0242 (6)
H23	−0.3873	0.2472	0.2912	0.029*
C24	−0.2399 (3)	0.19425 (17)	0.4073 (2)	0.0201 (6)
H24	−0.3090	0.1831	0.4667	0.024*
C25	−0.0897 (3)	0.17159 (16)	0.4240 (2)	0.0180 (6)
C26	0.0778 (3)	0.09022 (16)	0.5689 (2)	0.0173 (6)
C27	0.0723 (3)	0.04551 (18)	0.6760 (2)	0.0228 (6)
H27	−0.0181	0.0420	0.7166	0.027*
C28	0.1984 (3)	0.00719 (18)	0.7208 (2)	0.0255 (7)
H28	0.1970	−0.0226	0.7935	0.031*
C29	0.3296 (3)	0.01208 (18)	0.6589 (2)	0.0242 (6)
H29	0.4182	−0.0152	0.6876	0.029*
C210	0.3272 (3)	0.05701 (17)	0.5565 (2)	0.0227 (6)
H210	0.4172	0.0618	0.5156	0.027*
O1W	0.2013 (2)	0.40671 (13)	0.16781 (17)	0.0265 (5)
H1WA	0.197 (3)	0.4654 (5)	0.186 (2)	0.040*
H1WB	0.204 (3)	0.3763 (17)	0.2381 (14)	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01736 (17)	0.01915 (19)	0.01871 (18)	−0.00168 (13)	0.00328 (12)	−0.00258 (14)
O11	0.0260 (11)	0.0143 (10)	0.0287 (11)	−0.0055 (8)	0.0006 (8)	−0.0032 (8)
O12	0.0220 (11)	0.0287 (12)	0.0314 (11)	−0.0029 (9)	−0.0040 (9)	−0.0058 (9)
O13	0.0299 (11)	0.0186 (10)	0.0180 (10)	−0.0006 (8)	0.0080 (8)	−0.0018 (8)
O14	0.0357 (12)	0.0176 (11)	0.0284 (11)	0.0087 (9)	0.0061 (9)	−0.0021 (9)
N21	0.0192 (12)	0.0143 (12)	0.0180 (12)	−0.0003 (9)	0.0028 (9)	−0.0014 (9)
N22	0.0177 (12)	0.0263 (14)	0.0168 (12)	0.0004 (10)	0.0057 (9)	0.0050 (10)
N23	0.0182 (12)	0.0177 (12)	0.0200 (12)	0.0000 (9)	0.0009 (9)	−0.0011 (10)
C11	0.0259 (15)	0.0195 (15)	0.0158 (14)	−0.0055 (12)	0.0051 (11)	−0.0025 (12)
C12	0.0195 (14)	0.0193 (15)	0.0241 (15)	−0.0027 (12)	0.0006 (11)	−0.0029 (12)
C13	0.0182 (14)	0.0204 (15)	0.0182 (14)	−0.0023 (12)	0.0007 (11)	−0.0015 (12)
C14	0.0162 (13)	0.0191 (15)	0.0196 (14)	−0.0027 (11)	0.0033 (11)	0.0002 (12)
C15	0.0240 (15)	0.0202 (15)	0.0203 (15)	−0.0002 (12)	0.0055 (11)	0.0003 (12)
C16	0.0157 (13)	0.0235 (16)	0.0178 (15)	−0.0009 (12)	0.0001 (11)	−0.0028 (12)
C21	0.0259 (16)	0.0203 (15)	0.0223 (15)	0.0004 (12)	0.0069 (12)	0.0022 (12)
C22	0.0324 (17)	0.0268 (17)	0.0244 (16)	0.0056 (13)	0.0015 (13)	0.0066 (13)
C23	0.0201 (15)	0.0238 (16)	0.0288 (17)	0.0054 (12)	−0.0004 (12)	−0.0002 (13)
C24	0.0197 (14)	0.0191 (15)	0.0217 (14)	0.0000 (11)	0.0056 (11)	0.0000 (12)
C25	0.0226 (14)	0.0122 (13)	0.0193 (14)	−0.0002 (11)	0.0003 (11)	−0.0039 (11)
C26	0.0204 (14)	0.0142 (14)	0.0174 (14)	−0.0020 (11)	−0.0013 (11)	−0.0048 (11)
C27	0.0202 (14)	0.0274 (16)	0.0212 (15)	−0.0007 (12)	0.0055 (11)	0.0006 (12)
C28	0.0325 (17)	0.0252 (16)	0.0189 (15)	−0.0006 (13)	−0.0013 (12)	0.0042 (13)
C29	0.0237 (15)	0.0223 (16)	0.0264 (16)	0.0039 (13)	−0.0045 (12)	0.0016 (13)
C210	0.0174 (14)	0.0215 (16)	0.0292 (16)	0.0022 (11)	0.0025 (12)	−0.0015 (12)
O1W	0.0296 (11)	0.0208 (11)	0.0296 (12)	0.0023 (9)	0.0080 (9)	−0.0014 (9)

Geometric parameters (Å, º) top

Zn1—O11	2.0000 (18)	C14—C14ⁱⁱ	1.444 (5)
Zn1—N21	2.024 (2)	C14—H14	0.9500
Zn1—N23	2.067 (2)	C15—C16	1.489 (4)
Zn1—O13	2.0719 (18)	C15—H15	0.9500
Zn1—O14	2.3225 (19)	C21—C22	1.359 (4)
Zn1—C16	2.535 (3)	C21—H21	0.9500
O11—C11	1.284 (3)	C22—C23	1.390 (4)
O12—C11	1.242 (3)	C22—H22	0.9500
O13—C16	1.275 (3)	C23—C24	1.363 (4)
O14—C16	1.246 (3)	C23—H23	0.9500
N21—C25	1.346 (3)	C24—C25	1.402 (4)
N21—C21	1.356 (3)	C24—H24	0.9500
N22—C26	1.381 (3)	C26—C27	1.406 (4)
N22—C25	1.381 (3)	C27—C28	1.364 (4)
N22—H22N	0.8800	C27—H27	0.9500
N23—C26	1.335 (3)	C28—C29	1.396 (4)
N23—C210	1.362 (3)	C28—H28	0.9500
C11—C12	1.484 (3)	C29—C210	1.358 (4)
C12—C13	1.333 (4)	C29—H29	0.9500
C12—H12	0.9500	C210—H210	0.9500
C13—C13ⁱ	1.447 (5)	O1W—H1WA	0.929 (2)
C13—H13	0.9500	O1W—H1WB	0.930 (2)
C14—C15	1.335 (4)

O11—Zn1—N21	136.85 (8)	C14—C15—H15	118.0
O11—Zn1—N23	94.76 (8)	C16—C15—H15	118.0
N21—Zn1—N23	90.45 (8)	O14—C16—O13	120.2 (2)
O11—Zn1—O13	105.36 (7)	O14—C16—C15	120.0 (2)
N21—Zn1—O13	116.36 (8)	O13—C16—C15	119.8 (2)
N23—Zn1—O13	97.54 (8)	O14—C16—Zn1	65.86 (14)
O11—Zn1—O14	91.85 (7)	O13—C16—Zn1	54.45 (13)
N21—Zn1—O14	99.78 (8)	C15—C16—Zn1	173.3 (2)
N23—Zn1—O14	156.86 (8)	N21—C21—C22	123.2 (3)
O13—Zn1—O14	59.32 (7)	N21—C21—H21	118.4
O11—Zn1—C16	98.74 (8)	C22—C21—H21	118.4
N21—Zn1—C16	111.57 (8)	C21—C22—C23	119.0 (3)
N23—Zn1—C16	127.56 (9)	C21—C22—H22	120.5
O13—Zn1—C16	30.05 (8)	C23—C22—H22	120.5
O14—Zn1—C16	29.31 (7)	C24—C23—C22	119.2 (3)
C11—O11—Zn1	104.57 (17)	C24—C23—H23	120.4
C16—O13—Zn1	95.50 (16)	C22—C23—H23	120.4
C16—O14—Zn1	84.84 (16)	C23—C24—C25	119.2 (3)
C25—N21—C21	117.6 (2)	C23—C24—H24	120.4
C25—N21—Zn1	125.63 (18)	C25—C24—H24	120.4
C21—N21—Zn1	116.55 (18)	N21—C25—N22	121.8 (2)
C26—N22—C25	133.2 (2)	N21—C25—C24	121.8 (2)
C26—N22—H22N	113.4	N22—C25—C24	116.4 (2)
C25—N22—H22N	113.4	N23—C26—N22	120.7 (2)
C26—N23—C210	117.7 (2)	N23—C26—C27	121.8 (2)
C26—N23—Zn1	125.69 (18)	N22—C26—C27	117.5 (2)
C210—N23—Zn1	115.92 (18)	C28—C27—C26	119.2 (2)
O12—C11—O11	122.0 (2)	C28—C27—H27	120.4
O12—C11—C12	121.8 (2)	C26—C27—H27	120.4
O11—C11—C12	116.2 (2)	C27—C28—C29	119.5 (3)
C13—C12—C11	122.5 (2)	C27—C28—H28	120.3
C13—C12—H12	118.7	C29—C28—H28	120.3
C11—C12—H12	118.7	C210—C29—C28	118.2 (3)
C12—C13—C13ⁱ	124.5 (3)	C210—C29—H29	120.9
C12—C13—H13	117.8	C28—C29—H29	120.9
C13ⁱ—C13—H13	117.8	C29—C210—N23	123.7 (3)
C15—C14—C14ⁱⁱ	123.5 (3)	C29—C210—H210	118.2
C15—C14—H14	118.3	N23—C210—H210	118.2
C14ⁱⁱ—C14—H14	118.3	H1WA—O1W—H1WB	107 (3)
C14—C15—C16	124.0 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N22—H22N···O1Wⁱⁱⁱ	0.88	1.97	2.835 (3)	168
O1W—H1WB···O12	0.93 (1)	1.88 (1)	2.791 (3)	165 (3)
O1W—H1WA···O13^iv	0.93 (1)	1.89 (1)	2.816 (3)	172 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N22—H22N···O1Wⁱ	0.88	1.97	2.835 (3)	168.0
O1W—H1WB···O12	0.930 (2)	1.883 (9)	2.791 (3)	165 (3)
O1W—H1WA···O13ⁱⁱ	0.929 (2)	1.893 (5)	2.816 (3)	172 (3)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₆H₄O₄)(C₁₀H₉N₃)]·H₂O
M_r	394.68
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	170
a, b, c (Å)	8.9885 (13), 15.430 (2), 11.4182 (16)
β (°)	91.806 (2)
V (Å³)	1582.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.59
Crystal size (mm)	0.20 × 0.08 × 0.08

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8674, 3089, 2391
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.083, 0.91
No. of reflections	3089
No. of parameters	232
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.51

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), SHELXTL (Sheldrick, 2008).

Acknowledgements

Financial support from Kwangwoon University in the year 2016 is gratefully acknowledged.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 1| Part 4| April 2016| x160636

doi:10.1107/S2414314616006362

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