metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Di­aqua­bis­­{2-hy­dr­oxy-5-[(pyridin-2-yl)methyl­­idene­amino]­benzoato-κ2N,N′}zinc(II) dihydrate

aFaculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
*Correspondence e-mail: lix905@126.com

(Received 28 October 2010; accepted 2 November 2010; online 6 November 2010)

The complex mol­ecule of the title compound, [Zn(C13H9N2O3)2(H2O)2]·2H2O, has 2 symmetry with the ZnII cation located on a twofold rotation axis. The Zn cation is N,N′-chelated by two 5-[(pyridin-2-yl)methyl­idene­amino]-2-hy­droxy­benzoate anions and coordinated by two water mol­ecules in a distorted octa­hedral geometry. Within the anionic ligand, the pyridine ring is oriented at a dihedral angle of 49.54 (10)° with respect to the benzene ring. The carboxyl­ate group of the anionic ligand is not involved in coordination but is O—H⋯O hydrogen bonded to the coordinated and uncoordinated water mol­ecules. Weak inter­molecular C—H⋯O hydrogen bonding is also present in the crystal structure.

Related literature

The title compound is a Schiff base complex; for potential applications of Schiff base compounds, see: Bourque et al. (2005[Bourque, T. A., Nelles, M. E., Gullon, T. J., Garon, C. N., Ringer, M. K., Leger, L. J., Mason, J. W., Wheaton, S. L., Baerlocher, F. J., Vogels, C. M., Decken, A. & Westcott, S. A. (2005). Can. J. Chem. 83, 1063-1070.]); Donald & Osit (2010[Donald, J. D. & Osit, K. (2010). Inorg. Chem. 49, 2360-2371.]); Feng et al. (2007[Feng, L., Ji, Z. & Mohamedally, K. (2007). Inorg. Chem. 46, 8448-8450.]); Gang et al. (2007[Gang, W., Ian, J. H., Samir, M., Yanhua, L., Rodolphe, C., Christopher, E. A., Shilun, Q. & Annie, K. P. (2007). Inorg. Chem. 46, 7229-7231.]); Shanta et al. (2003[Shanta, D., Dulal, S., Puspendu, K. D., Pabitra, C., Munirathinam, N. & Akhil, R. C. (2003). J. Am. Chem. Soc. 125, 12118-12124.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C13H9N2O3)2(H2O)2]·2H2O

  • Mr = 619.90

  • Orthorhombic, P b c n

  • a = 15.812 (2) Å

  • b = 10.6962 (15) Å

  • c = 15.636 (2) Å

  • V = 2644.5 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.00 mm−1

  • T = 296 K

  • 0.43 × 0.32 × 0.27 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.689, Tmax = 0.764

  • 21797 measured reflections

  • 3041 independent reflections

  • 2291 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.083

  • S = 1.03

  • 3041 reflections

  • 206 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Selected bond lengths (Å)

Zn1—O1 2.0471 (15)
Zn1—N1 2.1414 (17)
Zn1—N2 2.2746 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O4i 0.80 (3) 1.83 (3) 2.618 (2) 169 (3)
O1—H2⋯O5 0.84 (3) 1.90 (3) 2.744 (3) 178 (3)
O5—H3⋯O3ii 0.86 (3) 1.98 (3) 2.808 (2) 161 (3)
O5—H4⋯O2iii 0.83 (3) 2.05 (3) 2.881 (3) 174 (3)
O2—H5⋯O3 0.95 (3) 1.58 (3) 2.473 (2) 156 (3)
C6—H6A⋯O2ii 0.93 2.57 3.346 (3) 142
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The current interest in design and synthesis of new Schiff bases and their metal complexes stem from their potential applications in antimicrobial (Bourque et al., 2005), magnetic (Feng et al., 2007; Gang et al., 2007), anticancer (Shanta et al., 2003) and catalytic (Donald et al., 2010). Hereby design and synthesis of new Schiff bases is a important field in coordination chemistry. 5-aminosalicylic acid is widely used in medicine and dye chemistry. 2-pyridinecarboxaldehyde is the intermeadiate of the bisacodyl, which is a popular medicine. We synthesized a new Schiff base 5-((pyridin-2-yl)methyleneamino)-2-hydroxybenzoic acid (C13H9N2O3) from 5-aminosalicylic acid and 2-pyridinecarboxaldehyde by nucleophilic addition, followed by a dehydration. The Schiff base can coordinate to the metal atoms through N or O donor atoms. Herein we report the preparation and characterization of the first 5-((pyridin-2-yl)methyleneamino)-2-hydroxybenzoic-zinc(II) complex, [Zn(C13H9N2O3)2(H2O)2].2H2O.

Single-crystal X-ray diffraction analysis indicates the title complex possesses a mononuclear structure and crystallizes in the orthorhombic, space group Pbcn with Z = 4. The asymmetric unit consists of two Schiff base ligand, one zinc ion, two coordinated water and two guest water molecule. A view of the zinc ion coordination is shown in Figure 1, where the metal center is coordinated in an octahedral geometry by four N atoms of the Schiff base ligand with Zn—N distances ranging from 2.1416 (17) to 2.2742 (14) Å and two O atoms from water molecules with Zn—O distances ranging from 2.0491 (15) Å. The intromolecular interaction is helpful to the stabilization of the crystal structure (Figure 2).

Related literature top

The title compound is a Schiff base complex; for potential applications of Schiff base compounds, see: Bourque et al. (2005); Donald & Osit (2010); Feng et al. (2007); Gang et al. (2007); Shanta et al. (2003).

Experimental top

5-Aminosalicylic acid (1.53 g, 10 mmol), 2-pyridinecarboxaldehyde (1 ml, 10 mmol) and triethylamine (1 ml, 10 mmol) were added to 50 ml e thanol in a round flask, and this mixture was refluxed with agitation for 4 h at 323 K to give an yellow precipitate. After filtration and washing the precipitate with ethanol to give the pure Schiff base 5-((pyridin-2-yl)methyleneamino)-2-hydroxybenzoic acid (2.02 g, 84.00%).

Mixture of 5-((pyridin-2-yl)methyleneamino)-2-hydroxybenzoic acid (0.1 mmol, 0.024 g), Zn(OAc)2.2H2O (0.1 mmol, 0.022 g) and methanol (20 ml) to give an yellow solution. After evaporating the solution for one week, yellow crystals were obtained (yield, 50%).

Refinement top

H atoms attached to C atoms were placed in calculated positions and treated using a riding-model approximation with C–H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms bonded to O atoms were located in a difference Fourier map and refined isotropically.

Structure description top

The current interest in design and synthesis of new Schiff bases and their metal complexes stem from their potential applications in antimicrobial (Bourque et al., 2005), magnetic (Feng et al., 2007; Gang et al., 2007), anticancer (Shanta et al., 2003) and catalytic (Donald et al., 2010). Hereby design and synthesis of new Schiff bases is a important field in coordination chemistry. 5-aminosalicylic acid is widely used in medicine and dye chemistry. 2-pyridinecarboxaldehyde is the intermeadiate of the bisacodyl, which is a popular medicine. We synthesized a new Schiff base 5-((pyridin-2-yl)methyleneamino)-2-hydroxybenzoic acid (C13H9N2O3) from 5-aminosalicylic acid and 2-pyridinecarboxaldehyde by nucleophilic addition, followed by a dehydration. The Schiff base can coordinate to the metal atoms through N or O donor atoms. Herein we report the preparation and characterization of the first 5-((pyridin-2-yl)methyleneamino)-2-hydroxybenzoic-zinc(II) complex, [Zn(C13H9N2O3)2(H2O)2].2H2O.

Single-crystal X-ray diffraction analysis indicates the title complex possesses a mononuclear structure and crystallizes in the orthorhombic, space group Pbcn with Z = 4. The asymmetric unit consists of two Schiff base ligand, one zinc ion, two coordinated water and two guest water molecule. A view of the zinc ion coordination is shown in Figure 1, where the metal center is coordinated in an octahedral geometry by four N atoms of the Schiff base ligand with Zn—N distances ranging from 2.1416 (17) to 2.2742 (14) Å and two O atoms from water molecules with Zn—O distances ranging from 2.0491 (15) Å. The intromolecular interaction is helpful to the stabilization of the crystal structure (Figure 2).

The title compound is a Schiff base complex; for potential applications of Schiff base compounds, see: Bourque et al. (2005); Donald & Osit (2010); Feng et al. (2007); Gang et al. (2007); Shanta et al. (2003).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the zinc ion coordination, showing the labeling of the non-H atoms and 30% probability ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Packing of title complex showing the three dimensional hydrogen bonding network.
Diaquabis{2-hydroxy-5-[(pyridin-2-yl)methylideneamino]benzoato- κ2N,N'}zinc(II) dihydrate top
Crystal data top
[Zn(C13H9N2O3)2(H2O)2]·2H2OF(000) = 1280
Mr = 619.90Dx = 1.557 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 5445 reflections
a = 15.812 (2) Åθ = 2.3–26.5°
b = 10.6962 (15) ŵ = 1.00 mm1
c = 15.636 (2) ÅT = 296 K
V = 2644.5 (6) Å3Block, yellow
Z = 40.43 × 0.32 × 0.27 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3041 independent reflections
Radiation source: fine-focus sealed tube2291 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2020
Tmin = 0.689, Tmax = 0.764k = 1313
21797 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0389P)2 + 0.7619P]
where P = (Fo2 + 2Fc2)/3
3041 reflections(Δ/σ)max < 0.001
206 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[Zn(C13H9N2O3)2(H2O)2]·2H2OV = 2644.5 (6) Å3
Mr = 619.90Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 15.812 (2) ŵ = 1.00 mm1
b = 10.6962 (15) ÅT = 296 K
c = 15.636 (2) Å0.43 × 0.32 × 0.27 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3041 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
2291 reflections with I > 2σ(I)
Tmin = 0.689, Tmax = 0.764Rint = 0.038
21797 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.33 e Å3
3041 reflectionsΔρmin = 0.29 e Å3
206 parameters
Special details top

Experimental. IR (KBr, cm-1): 3455(versus), 3088(w), 2924(w), 2361(w), 1919(w), 1668(s), 1602(m), 1578(m), 1489(versus), 1447(m), 1364(versus), 1299(m), 1245(s), 1161(m), 1084(m), 1054(s), 959(w), 893(m), 839(s), 792(versus), 655(m), 572(m), 512(m).

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.50000.40959 (2)0.25000.03779 (10)
O10.49550 (12)0.53276 (14)0.14990 (11)0.0590 (4)
O20.70387 (10)0.06373 (16)0.00402 (11)0.0623 (4)
O30.62843 (10)0.24718 (13)0.05467 (11)0.0670 (4)
O40.51579 (10)0.22474 (13)0.13984 (11)0.0615 (4)
O50.37521 (14)0.47962 (17)0.02876 (13)0.0709 (5)
N10.36496 (10)0.39448 (14)0.24957 (9)0.0414 (4)
N20.47286 (10)0.24704 (13)0.16032 (9)0.0364 (3)
C10.31145 (14)0.4780 (2)0.28233 (14)0.0525 (5)
H1A0.33290.54400.31440.063*
C20.22455 (15)0.4697 (2)0.27010 (15)0.0625 (6)
H2A0.18890.53110.29190.075*
C30.19182 (15)0.3703 (2)0.22564 (16)0.0643 (6)
H3A0.13370.36150.21900.077*
C40.24669 (13)0.2838 (2)0.19101 (14)0.0537 (5)
H4A0.22620.21580.16030.064*
C50.33299 (12)0.30015 (17)0.20284 (12)0.0416 (4)
C60.39452 (12)0.21815 (16)0.16127 (12)0.0415 (4)
H6A0.37650.14450.13540.050*
C70.53077 (12)0.16496 (16)0.11906 (11)0.0363 (4)
C80.59723 (12)0.21657 (17)0.07233 (12)0.0458 (4)
H8A0.60340.30290.06950.055*
C90.65391 (13)0.14022 (19)0.03025 (13)0.0507 (5)
H9A0.69770.17530.00140.061*
C100.64583 (12)0.01035 (18)0.03502 (13)0.0444 (4)
C110.57989 (11)0.04244 (16)0.08294 (12)0.0386 (4)
C120.52303 (11)0.03585 (16)0.12417 (11)0.0374 (4)
H12A0.47900.00130.15580.045*
C130.57306 (13)0.18215 (17)0.09375 (13)0.0470 (5)
H10.5058 (16)0.606 (3)0.152 (2)0.081 (10)*
H20.4595 (18)0.517 (3)0.1115 (18)0.083 (9)*
H30.3812 (19)0.417 (3)0.005 (2)0.084 (9)*
H40.326 (2)0.507 (3)0.025 (2)0.124 (14)*
H50.685 (2)0.146 (3)0.009 (2)0.117 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04294 (17)0.02329 (15)0.04715 (18)0.0000.00043 (13)0.000
O10.0828 (11)0.0317 (8)0.0625 (9)0.0157 (8)0.0203 (9)0.0127 (7)
O20.0562 (9)0.0523 (9)0.0785 (11)0.0026 (7)0.0186 (8)0.0231 (8)
O30.0642 (9)0.0356 (8)0.1011 (12)0.0057 (7)0.0064 (9)0.0178 (8)
O40.0744 (11)0.0280 (7)0.0820 (11)0.0052 (7)0.0102 (8)0.0028 (7)
O50.0746 (12)0.0529 (10)0.0851 (12)0.0051 (9)0.0225 (10)0.0171 (9)
N10.0442 (8)0.0357 (8)0.0443 (8)0.0064 (6)0.0028 (7)0.0041 (7)
N20.0446 (8)0.0241 (7)0.0406 (8)0.0009 (6)0.0000 (6)0.0006 (6)
C10.0608 (13)0.0453 (12)0.0514 (11)0.0133 (10)0.0115 (10)0.0046 (9)
C20.0562 (13)0.0630 (15)0.0684 (15)0.0221 (11)0.0210 (11)0.0172 (12)
C30.0452 (12)0.0712 (16)0.0764 (15)0.0103 (11)0.0067 (11)0.0232 (13)
C40.0462 (11)0.0533 (12)0.0616 (13)0.0023 (9)0.0050 (10)0.0108 (10)
C50.0427 (10)0.0356 (9)0.0466 (10)0.0005 (8)0.0012 (8)0.0081 (8)
C60.0466 (11)0.0302 (9)0.0477 (10)0.0031 (8)0.0059 (8)0.0008 (8)
C70.0402 (9)0.0283 (9)0.0404 (9)0.0013 (7)0.0009 (8)0.0014 (7)
C80.0593 (12)0.0284 (9)0.0497 (10)0.0078 (8)0.0067 (9)0.0001 (8)
C90.0572 (12)0.0423 (11)0.0525 (11)0.0125 (9)0.0166 (10)0.0025 (9)
C100.0457 (10)0.0416 (10)0.0459 (10)0.0015 (8)0.0015 (9)0.0118 (8)
C110.0429 (10)0.0285 (8)0.0443 (10)0.0031 (7)0.0054 (8)0.0039 (7)
C120.0394 (9)0.0290 (9)0.0438 (10)0.0047 (7)0.0017 (7)0.0000 (7)
C130.0533 (12)0.0284 (9)0.0593 (12)0.0014 (8)0.0092 (10)0.0067 (9)
Geometric parameters (Å, º) top
Zn1—O1i2.0471 (15)C1—H1A0.9300
Zn1—O12.0471 (15)C2—C31.372 (4)
Zn1—N1i2.1414 (17)C2—H2A0.9300
Zn1—N12.1414 (17)C3—C41.379 (3)
Zn1—N22.2746 (14)C3—H3A0.9300
Zn1—N2i2.2746 (14)C4—C51.388 (3)
O1—H10.81 (3)C4—H4A0.9300
O1—H20.84 (3)C5—C61.462 (3)
O2—C101.357 (2)C6—H6A0.9300
O2—H50.95 (3)C7—C121.389 (2)
O3—C131.274 (2)C7—C81.394 (3)
O4—C131.244 (2)C8—C91.380 (3)
O5—H30.86 (3)C8—H8A0.9300
O5—H40.84 (4)C9—C101.397 (3)
N1—C11.333 (2)C9—H9A0.9300
N1—C51.344 (2)C10—C111.403 (3)
N2—C61.277 (2)C11—C121.388 (2)
N2—C71.423 (2)C11—C131.508 (2)
C1—C21.390 (3)C12—H12A0.9300
O1i—Zn1—O199.88 (10)C2—C3—H3A120.6
O1i—Zn1—N1i90.66 (6)C4—C3—H3A120.6
O1—Zn1—N1i94.92 (7)C3—C4—C5118.8 (2)
O1i—Zn1—N194.92 (7)C3—C4—H4A120.6
O1—Zn1—N190.66 (6)C5—C4—H4A120.6
N1i—Zn1—N1171.34 (8)N1—C5—C4122.45 (18)
O1i—Zn1—N2165.91 (6)N1—C5—C6116.20 (16)
O1—Zn1—N290.80 (6)C4—C5—C6121.29 (18)
N1i—Zn1—N297.61 (5)N2—C6—C5120.37 (16)
N1—Zn1—N275.65 (6)N2—C6—H6A119.8
O1i—Zn1—N2i90.80 (6)C5—C6—H6A119.8
O1—Zn1—N2i165.91 (6)C12—C7—C8119.37 (17)
N1i—Zn1—N2i75.65 (6)C12—C7—N2122.05 (16)
N1—Zn1—N2i97.61 (5)C8—C7—N2118.58 (15)
N2—Zn1—N2i80.29 (7)C9—C8—C7120.36 (17)
Zn1—O1—H1126 (2)C9—C8—H8A119.8
Zn1—O1—H2115.9 (19)C7—C8—H8A119.8
H1—O1—H2111 (3)C8—C9—C10120.25 (17)
C10—O2—H5103 (2)C8—C9—H9A119.9
H3—O5—H4109 (3)C10—C9—H9A119.9
C1—N1—C5118.25 (18)O2—C10—C9119.64 (18)
C1—N1—Zn1125.53 (15)O2—C10—C11120.52 (18)
C5—N1—Zn1115.68 (12)C9—C10—C11119.79 (17)
C6—N2—C7118.70 (15)C12—C11—C10119.14 (16)
C6—N2—Zn1111.15 (12)C12—C11—C13119.98 (17)
C7—N2—Zn1129.02 (12)C10—C11—C13120.80 (17)
N1—C1—C2122.1 (2)C11—C12—C7121.09 (17)
N1—C1—H1A118.9C11—C12—H12A119.5
C2—C1—H1A118.9C7—C12—H12A119.5
C3—C2—C1119.5 (2)O4—C13—O3125.32 (18)
C3—C2—H2A120.3O4—C13—C11118.69 (17)
C1—C2—H2A120.3O3—C13—C11115.98 (18)
C2—C3—C4118.8 (2)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4ii0.80 (3)1.83 (3)2.618 (2)169 (3)
O1—H2···O50.84 (3)1.90 (3)2.744 (3)178 (3)
O5—H3···O3iii0.86 (3)1.98 (3)2.808 (2)161 (3)
O5—H4···O2iv0.83 (3)2.05 (3)2.881 (3)174 (3)
O2—H5···O30.95 (3)1.58 (3)2.473 (2)156 (3)
C6—H6A···O2iii0.932.573.346 (3)142
Symmetry codes: (ii) x, y+1, z; (iii) x+1, y, z; (iv) x1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula[Zn(C13H9N2O3)2(H2O)2]·2H2O
Mr619.90
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)296
a, b, c (Å)15.812 (2), 10.6962 (15), 15.636 (2)
V3)2644.5 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.00
Crystal size (mm)0.43 × 0.32 × 0.27
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.689, 0.764
No. of measured, independent and
observed [I > 2σ(I)] reflections
21797, 3041, 2291
Rint0.038
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.083, 1.03
No. of reflections3041
No. of parameters206
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.29

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Zn1—O12.0471 (15)Zn1—N22.2746 (14)
Zn1—N12.1414 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.80 (3)1.83 (3)2.618 (2)169 (3)
O1—H2···O50.84 (3)1.90 (3)2.744 (3)178 (3)
O5—H3···O3ii0.86 (3)1.98 (3)2.808 (2)161 (3)
O5—H4···O2iii0.83 (3)2.05 (3)2.881 (3)174 (3)
O2—H5···O30.95 (3)1.58 (3)2.473 (2)156 (3)
C6—H6A···O2ii0.932.573.346 (3)142
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x1/2, y+1/2, z.
 

Acknowledgements

The work was supported by the Ningbo Natural Science Foundation (2010 A610060), the `Qianjiang Talent' Projects of Zhejiang Province (2009R10032), the Ningbo University Foundation (XK1066), the Program for Innovative Research Team of Ningbo Novel Photoelectric Materials and Devices (2009B21007) and the K. C. Wong Magna Fund of Ningbo University.

References

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