metal-organic compounds
catena-Poly[[[[bis(pyridin-2-yl-κN)amine]zinc(II)]-μ2-(2E,4E)-hexa-2,4-dienedioato-κ4O1,O1′:O6,O6′] monohydrate]
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
In the title compound, {[Zn(C6H4O4)(C10H9N3)]·H2O}n, the di(pyridin-2-yl)amine (dpa) ligands chelate the ZnII 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 ZnII ions in asymmetric chelating modes. The ZnII 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
Structure description
Metal–organic frameworks (MOFs), constructed from metal ions and polytopic bridging ligands, have been used for selective gas sorption, 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 of the title compound.
separation, sensors, drug delivery and biological imaging. Dicarboxylates have provided structures of various dimensionalities with different coordination modes and pore sizes. Rigid aromatic dicarboxylates (SumidaA fragment of the one-dimensional title compound, in which 2,2′-dipyridylamine ligands chelate ZnII 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 ZnII 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 ZnII 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).
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 .
details are summarized in Table 2Structural data
CCDC reference: 1474269
10.1107/S2414314616006362/lh4006sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616006362/lh4006Isup2.hkl
Metal–organic frameworks (MOFs) have been constructed by metal ions and polytopic bridging ligands, and used for selective gas sorption, 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 of the title compound.
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,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).
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.
Crystal data, data collection and structure
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 in riding-motion approximation with Uiso(H) = 1.2Ueq(C) and 1.2Ueq(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 Uiso(H) = 1.5Ueq(O).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.
Metal–organic frameworks (MOFs), constructed from metal ions and polytopic bridging ligands, have been used for selective gas sorption, 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 of the title compound.
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,A fragment of the one-dimensional title compound, in which 2,2'-dipyridylaime ligands chelate ZnII 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 ZnII 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 ZnII 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).
Data collection: SMART (Bruker, 1997); cell
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).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. |
[Zn(C6H4O4)(C10H9N3)]·H2O | F(000) = 808 |
Mr = 394.68 | Dx = 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 |
Bruker APEX CCD diffractometer | Rint = 0.074 |
φ and ω scans | θmax = 26.0°, θmin = 2.2° |
8674 measured reflections | h = −11→10 |
3089 independent reflections | k = −17→19 |
2391 reflections with I > 2σ(I) | l = −14→14 |
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(Fo2) + (0.0386P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max < 0.001 |
3089 reflections | Δρmax = 0.82 e Å−3 |
232 parameters | Δρmin = −0.51 e Å−3 |
[Zn(C6H4O4)(C10H9N3)]·H2O | V = 1582.8 (4) Å3 |
Mr = 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)° |
Bruker APEX CCD diffractometer | 2391 reflections with I > 2σ(I) |
8674 measured reflections | Rint = 0.074 |
3089 independent reflections |
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 | Δρmax = 0.82 e Å−3 |
3089 reflections | Δρmin = −0.51 e Å−3 |
232 parameters |
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 | ||
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* |
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) |
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. |
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···O13iv | 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. |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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
Hwang, I. H., Bae, J. M., Kim, W.-S., Jo, Y. D., Kim, C., Kim, Y., Kim, S.-J. & Huh, S. (2012). Dalton Trans. 41, 12759–12765. Web of Science CSD CrossRef CAS PubMed Google Scholar
Hwang, I. H., Kim, H.-Y., Lee, M. M., Na, Y. J., Kim, J. H., Kim, H.-C., Kim, C., Huh, S., Kim, Y. & Kim, S.-J. (2013). Cryst. Growth Des. 13, 4815–4823. Web of Science CSD CrossRef CAS Google Scholar
Hyun, M. Y., Hwang, I. H., Lee, M. M., Kim, H., Kim, K. B., Kim, C., Kim, H.-Y., Kim, Y. & Kim, S.-J. (2013). Polyhedron, 53, 166–171. CSD CrossRef CAS Google Scholar
Kim, E. Y., Park, H. M., Kim, H.-Y., Kim, J. H., Hyun, M. Y., Lee, J. H., Kim, C., Kim, S.-J. & Kim, Y. (2011). J. Mol. Struct. 994, 335–342. Web of Science CSD CrossRef CAS Google Scholar
Lee, M. M., Kim, H.-Y., Hwang, I. H., Bae, J. M., Kim, C., Yo, C.-H., Kim, Y. & Kim, S.-J. (2014). Bull. Korean Chem. Soc. 35, 1777–1783. CrossRef CAS Google Scholar
Lee, Y. J., Kim, E. Y., Kim, S. H., Jang, S. P., Lee, T. G., Kim, C., Kim, S.-J. & Kim, Y. (2011). New J. Chem. 35, 833–841. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sumida, K., Rogow, D. L., Mason, J. A., McDonald, T. M., Bloch, E. D., Herm, Z. R., Bae, T.-H. & Long, J. R. (2012). Chem. Rev. 112, 724–781. Web of Science CrossRef CAS PubMed Google Scholar
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