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In the title complex, [Zn(C20H14N2O4)(H2O)]·3H2O, the ZnII center is in an approximately square-pyramidal coordination environment with the two N and two O atoms of the tetra­dentate Schiff base ligand forming the basal plane and the coordinated water mol­ecule in the apical position. Three solvent water mol­ecules complete the asymmetric unit. The dihedral angles between the two outer benzene rings of the Schiff base and the central benzene ring are 12.64 (14) and 17.25 (14)°. In the crystal structure, inter­molecular O—H...O hydrogen bonds link the mol­ecules into sheets parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052713/sj2387sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052713/sj2387Isup2.hkl
Contains datablock I

CCDC reference: 667235

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.088
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H4B .. H4B .. 1.17 Ang.
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 5 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 2.09 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Zinc is an element attracting strong interests in biology, medicine, materials, and catalysis. It plays important roles in various biological systems such as neurotransmission, signal transduction, and gene expression (Assaf & Chung, 1984; Berg & Shi, 1996). It is well known that zinc complexes with Schiff-bases are biologically active and show very good cytotoxicity against the leukemic cell (Tarafder et al., 2002). Since our previous investigations (Eltayeb et al., 2007a, b, c, d) show the possibility of generating five coordinate zinc complexes using tetradentate Schiff base ligands, we have extended our synthesis to the title complex and report its crystal structure here.

In the title complex (Fig. 1), ZnII coordinates with the tetradentate Schiff base ligand in the basal plane (N1, N2, O1 and O2) and a water molecule in the apical site. The ZnII center lies slightly above the N2O2 plane in a geometry that is roughly square pyramidal, with the Zn in the Zn—N2O2 plane being tilted 0.01190 Å towards the axial water molecule. This geometry has been observed for similar Schiff base ligand ZnII complexes (Eltayeb et al., 2007a, b, c, d). The dihedral angles between the two benzene rings (C1–C6) and (C15–C20) and the central benzene ring (C8–C13) are 12.64 (14)° and 17.25 (14) °, respectively. The Zn1—N1 and Zn1—N2 distances of 2.069 (2) Å and 2.075 (2) Å and bond angles around Zn1 are in agreement with the values found for similar ZnII complexes (Eltayeb et al., 2007a, b, c, d). However, the Zn1—O1 and Zn1—O2 distances, 1.9905 (19) and 2.001 (2) Å, respectively are slightly shorter than those observed in a closely related structure (Eltayeb ey al., 2007 d) where the Zn—O distances are in the range 2.0027 (15)–2.0036 (15) Å. All water molecules are involved in intermolecular O—H···O hydrogen bonds. Bond lengths and angles observed in the structure are normal (Allen et al., 1987).

In the crystal packing (Fig. 2), O—H···O hydrogen bonds (Table 1) link the molecules into sheets parallel to the ab plane.

Related literature top

For bond-length data, see Allen et al. (1987). For related structures, see for example: Chaudhuri et al. (2007); Eltayeb et al. (2007a,b,c,d). For background information on the biological activity of zinc and its complexes, see for example: Assaf & Chung (1984); Berg & Shi (1996); Tarafder et al. (2002).

Experimental top

The title compound (I) was synthesized by adding 2,4-dihydroxybenzaldehyde (0.552 g, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (20 ml). The mixture was refluxed with stirring for an hour. Then zinc chloride (0.272 g, 2 mmol) in ethanol (10 ml) was added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was stirred at room temperature for two hours. A yellow precipitate was obtained, washed with about 5 ml e thanol, dried, and then with copious amounts of diethyl ether. This precipitate was dissolved in 20 ml of acetone and, after evaporation of the acetone, the powder obtained was dissolved in diethyl ether. Single crystals of the title compound suitable for x-ray structure determination were formed after several days of slow evaporation of the diethyl ether at room temperature.

Refinement top

The H atom (H1W3) was located from the difference map and was refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93 Å and an O—H distance of 0.85 Å and the Uiso values were constrained to be 1.2Ueq(C) and 1.5Ueq(O). The highest residual electron density peak is located 0.94 Å from O4W and the deepest hole is located 0.87 Å from Zn1.

Structure description top

Zinc is an element attracting strong interests in biology, medicine, materials, and catalysis. It plays important roles in various biological systems such as neurotransmission, signal transduction, and gene expression (Assaf & Chung, 1984; Berg & Shi, 1996). It is well known that zinc complexes with Schiff-bases are biologically active and show very good cytotoxicity against the leukemic cell (Tarafder et al., 2002). Since our previous investigations (Eltayeb et al., 2007a, b, c, d) show the possibility of generating five coordinate zinc complexes using tetradentate Schiff base ligands, we have extended our synthesis to the title complex and report its crystal structure here.

In the title complex (Fig. 1), ZnII coordinates with the tetradentate Schiff base ligand in the basal plane (N1, N2, O1 and O2) and a water molecule in the apical site. The ZnII center lies slightly above the N2O2 plane in a geometry that is roughly square pyramidal, with the Zn in the Zn—N2O2 plane being tilted 0.01190 Å towards the axial water molecule. This geometry has been observed for similar Schiff base ligand ZnII complexes (Eltayeb et al., 2007a, b, c, d). The dihedral angles between the two benzene rings (C1–C6) and (C15–C20) and the central benzene ring (C8–C13) are 12.64 (14)° and 17.25 (14) °, respectively. The Zn1—N1 and Zn1—N2 distances of 2.069 (2) Å and 2.075 (2) Å and bond angles around Zn1 are in agreement with the values found for similar ZnII complexes (Eltayeb et al., 2007a, b, c, d). However, the Zn1—O1 and Zn1—O2 distances, 1.9905 (19) and 2.001 (2) Å, respectively are slightly shorter than those observed in a closely related structure (Eltayeb ey al., 2007 d) where the Zn—O distances are in the range 2.0027 (15)–2.0036 (15) Å. All water molecules are involved in intermolecular O—H···O hydrogen bonds. Bond lengths and angles observed in the structure are normal (Allen et al., 1987).

In the crystal packing (Fig. 2), O—H···O hydrogen bonds (Table 1) link the molecules into sheets parallel to the ab plane.

For bond-length data, see Allen et al. (1987). For related structures, see for example: Chaudhuri et al. (2007); Eltayeb et al. (2007a,b,c,d). For background information on the biological activity of zinc and its complexes, see for example: Assaf & Chung (1984); Berg & Shi (1996); Tarafder et al. (2002).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Hydrogen bonds are drawn as dashed lines.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.
Aqua{5,5'-dihydroxy-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato- κ4O,N,N',O'}zinc(II) trihydrate top
Crystal data top
[Zn(C20H14N2O4)(H2O)]·3H2OZ = 2
Mr = 483.77F(000) = 500
Triclinic, P1Dx = 1.641 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.7462 (1) ÅCell parameters from 3830 reflections
b = 13.9290 (2) Åθ = 1.9–26.0°
c = 15.1128 (2) ŵ = 1.31 mm1
α = 82.147 (1)°T = 100 K
β = 82.367 (1)°Needle, brown
γ = 85.640 (1)°0.45 × 0.44 × 0.06 mm
V = 979.26 (3) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
3830 independent reflections
Radiation source: fine-focus sealed tube3151 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 1.9°
ω scansh = 55
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1717
Tmin = 0.591, Tmax = 0.928l = 1818
13930 measured reflections
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0324P)2 + 1.1626P]
where P = (Fo2 + 2Fc2)/3
3830 reflections(Δ/σ)max = 0.001
283 parametersΔρmax = 0.40 e Å3
1 restraintΔρmin = 0.49 e Å3
Crystal data top
[Zn(C20H14N2O4)(H2O)]·3H2Oγ = 85.640 (1)°
Mr = 483.77V = 979.26 (3) Å3
Triclinic, P1Z = 2
a = 4.7462 (1) ÅMo Kα radiation
b = 13.9290 (2) ŵ = 1.31 mm1
c = 15.1128 (2) ÅT = 100 K
α = 82.147 (1)°0.45 × 0.44 × 0.06 mm
β = 82.367 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
3830 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3151 reflections with I > 2σ(I)
Tmin = 0.591, Tmax = 0.928Rint = 0.042
13930 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.40 e Å3
3830 reflectionsΔρmin = 0.49 e Å3
283 parameters
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Zn10.30697 (8)0.72049 (2)0.26300 (2)0.01785 (11)
O10.5818 (5)0.60560 (14)0.28209 (13)0.0254 (5)
O20.4864 (4)0.79828 (13)0.33907 (13)0.0212 (5)
O31.0486 (5)0.29375 (14)0.25981 (14)0.0261 (5)
H3A1.10550.30460.30620.039*
O40.8766 (5)1.06174 (14)0.43613 (13)0.0246 (5)
H4B0.93531.01620.47060.037*
N10.1980 (5)0.66784 (16)0.15136 (15)0.0185 (5)
N20.1532 (5)0.84744 (16)0.19188 (15)0.0169 (5)
C10.6230 (6)0.5270 (2)0.24088 (18)0.0189 (6)
C20.8138 (7)0.4521 (2)0.27199 (19)0.0212 (6)
H2A0.90830.45930.32060.025*
C30.8651 (7)0.3675 (2)0.23203 (19)0.0206 (6)
C40.7266 (7)0.3553 (2)0.1590 (2)0.0256 (7)
H4A0.76080.29890.13180.031*
C50.5405 (7)0.4273 (2)0.1279 (2)0.0249 (7)
H5A0.44770.41850.07940.030*
C60.4823 (6)0.5148 (2)0.16609 (18)0.0186 (6)
C70.2848 (7)0.5843 (2)0.12562 (19)0.0209 (7)
H7A0.21130.56800.07590.025*
C80.0170 (6)0.7336 (2)0.10196 (18)0.0171 (6)
C90.1341 (7)0.7108 (2)0.03546 (19)0.0212 (7)
H9A0.12560.64720.02260.025*
C100.2963 (7)0.7814 (2)0.01161 (19)0.0229 (7)
H10A0.39210.76580.05700.027*
C110.3156 (7)0.8755 (2)0.00914 (19)0.0226 (7)
H11A0.42630.92280.02230.027*
C120.1730 (7)0.9001 (2)0.07570 (18)0.0210 (6)
H12A0.18960.96360.08910.025*
C130.0037 (6)0.8303 (2)0.12306 (18)0.0170 (6)
C140.2075 (6)0.9345 (2)0.20311 (18)0.0188 (6)
H14A0.12720.98530.16620.023*
C150.3774 (6)0.96045 (19)0.26622 (18)0.0171 (6)
C160.4182 (7)1.0602 (2)0.26370 (19)0.0213 (7)
H16A0.32861.10450.22300.026*
C170.5840 (7)1.0945 (2)0.3185 (2)0.0246 (7)
H17A0.60951.16060.31440.030*
C180.7142 (6)1.0281 (2)0.38088 (18)0.0189 (6)
C190.6798 (6)0.9299 (2)0.38556 (18)0.0188 (6)
H19A0.76970.88690.42710.023*
C200.5135 (6)0.89341 (19)0.32953 (18)0.0165 (6)
O1W0.0108 (5)0.67205 (17)0.35940 (14)0.0328 (6)
H2W10.10940.63040.34350.049*
H1W10.11750.72320.36510.049*
O2W0.2688 (6)0.50060 (16)0.45460 (16)0.0441 (7)
H1W20.31300.54790.41460.066*
H2W20.23410.52250.50500.066*
O3W0.2523 (5)0.31908 (15)0.41217 (14)0.0268 (5)
H2W30.26900.37720.42160.040*
H1W30.400 (6)0.289 (2)0.429 (2)0.040*
O4W0.2536 (5)0.75935 (14)0.51765 (13)0.0250 (5)
H1W40.23890.81980.52200.037*
H2W40.30540.75270.46270.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0192 (2)0.01691 (18)0.01923 (18)0.00110 (14)0.00642 (14)0.00494 (12)
O10.0318 (13)0.0187 (10)0.0301 (11)0.0039 (10)0.0159 (10)0.0103 (9)
O20.0263 (12)0.0143 (10)0.0257 (10)0.0019 (9)0.0108 (10)0.0045 (8)
O30.0284 (13)0.0196 (11)0.0317 (11)0.0047 (10)0.0092 (10)0.0064 (9)
O40.0263 (13)0.0205 (11)0.0310 (11)0.0017 (10)0.0142 (10)0.0074 (9)
N10.0186 (14)0.0172 (12)0.0208 (12)0.0036 (11)0.0041 (11)0.0035 (10)
N20.0152 (13)0.0186 (12)0.0192 (12)0.0008 (10)0.0063 (10)0.0064 (9)
C10.0182 (16)0.0177 (14)0.0208 (14)0.0032 (13)0.0006 (13)0.0033 (11)
C20.0222 (17)0.0214 (15)0.0218 (14)0.0029 (13)0.0070 (13)0.0045 (12)
C30.0193 (16)0.0156 (14)0.0250 (15)0.0007 (13)0.0023 (13)0.0010 (11)
C40.0306 (19)0.0208 (15)0.0277 (16)0.0002 (14)0.0037 (15)0.0116 (12)
C50.0272 (18)0.0268 (16)0.0234 (15)0.0002 (14)0.0074 (14)0.0088 (13)
C60.0175 (16)0.0190 (14)0.0200 (14)0.0028 (13)0.0022 (13)0.0041 (11)
C70.0224 (17)0.0219 (15)0.0211 (14)0.0056 (13)0.0060 (13)0.0070 (12)
C80.0141 (15)0.0207 (14)0.0169 (13)0.0032 (12)0.0020 (12)0.0022 (11)
C90.0227 (17)0.0186 (14)0.0236 (15)0.0048 (13)0.0046 (13)0.0037 (12)
C100.0211 (17)0.0291 (16)0.0204 (14)0.0040 (14)0.0068 (13)0.0047 (12)
C110.0216 (17)0.0257 (16)0.0204 (14)0.0006 (14)0.0051 (13)0.0017 (12)
C120.0203 (17)0.0226 (15)0.0206 (14)0.0014 (13)0.0021 (13)0.0047 (12)
C130.0140 (15)0.0211 (14)0.0160 (13)0.0038 (12)0.0009 (12)0.0027 (11)
C140.0176 (16)0.0192 (14)0.0192 (14)0.0015 (13)0.0028 (13)0.0023 (11)
C150.0167 (16)0.0174 (14)0.0175 (13)0.0021 (12)0.0002 (12)0.0042 (11)
C160.0245 (17)0.0172 (14)0.0228 (15)0.0003 (13)0.0086 (13)0.0005 (12)
C170.0326 (19)0.0144 (14)0.0294 (16)0.0029 (14)0.0104 (15)0.0043 (12)
C180.0169 (16)0.0195 (14)0.0221 (14)0.0038 (13)0.0040 (13)0.0066 (12)
C190.0185 (16)0.0177 (14)0.0215 (14)0.0010 (13)0.0069 (13)0.0033 (11)
C200.0152 (15)0.0145 (13)0.0206 (14)0.0002 (12)0.0013 (12)0.0060 (11)
O1W0.0326 (14)0.0409 (13)0.0280 (12)0.0171 (11)0.0019 (11)0.0126 (10)
O2W0.070 (2)0.0225 (12)0.0439 (14)0.0046 (13)0.0254 (14)0.0063 (10)
O3W0.0268 (13)0.0195 (11)0.0361 (12)0.0014 (10)0.0103 (11)0.0053 (9)
O4W0.0329 (13)0.0201 (10)0.0241 (11)0.0022 (10)0.0083 (10)0.0053 (8)
Geometric parameters (Å, º) top
Zn1—O21.9905 (19)C9—C101.380 (4)
Zn1—O12.001 (2)C9—H9A0.9300
Zn1—O1W2.038 (2)C10—C111.382 (4)
Zn1—N12.069 (2)C10—H10A0.9300
Zn1—N22.075 (2)C11—C121.378 (4)
O1—C11.322 (3)C11—H11A0.9300
O2—C201.327 (3)C12—C131.396 (4)
O3—C31.354 (3)C12—H12A0.9300
O3—H3A0.8200C14—C151.426 (4)
O4—C181.358 (3)C14—H14A0.9300
O4—H4B0.8200C15—C161.412 (4)
N1—C71.298 (3)C15—C201.426 (4)
N1—C81.414 (4)C16—C171.368 (4)
N2—C141.296 (3)C16—H16A0.9300
N2—C131.412 (3)C17—C181.398 (4)
C1—C21.402 (4)C17—H17A0.9300
C1—C61.422 (4)C18—C191.381 (4)
C2—C31.387 (4)C19—C201.399 (4)
C2—H2A0.9300C19—H19A0.9300
C3—C41.393 (4)O1W—H2W10.8501
C4—C51.361 (4)O1W—H1W10.8500
C4—H4A0.9300O2W—H1W20.8498
C5—C61.411 (4)O2W—H2W20.8499
C5—H5A0.9300O3W—H2W30.8516
C6—C71.429 (4)O3W—H1W30.838 (18)
C7—H7A0.9300O4W—H1W40.8499
C8—C91.392 (4)O4W—H2W40.8499
C8—C131.419 (4)
O2—Zn1—O193.81 (8)N1—C8—C13115.4 (2)
O2—Zn1—O1W96.57 (8)C10—C9—C8120.9 (3)
O1—Zn1—O1W97.05 (10)C10—C9—H9A119.6
O2—Zn1—N1161.27 (9)C8—C9—H9A119.6
O1—Zn1—N189.57 (8)C9—C10—C11119.6 (3)
O1W—Zn1—N1101.29 (9)C9—C10—H10A120.2
O2—Zn1—N290.02 (8)C11—C10—H10A120.2
O1—Zn1—N2154.17 (9)C12—C11—C10120.9 (3)
O1W—Zn1—N2107.88 (10)C12—C11—H11A119.5
N1—Zn1—N279.23 (9)C10—C11—H11A119.5
C1—O1—Zn1129.69 (18)C11—C12—C13120.4 (3)
C20—O2—Zn1129.08 (17)C11—C12—H12A119.8
C3—O3—H3A109.5C13—C12—H12A119.8
C18—O4—H4B109.5C12—C13—N2125.2 (3)
C7—N1—C8121.3 (2)C12—C13—C8118.9 (3)
C7—N1—Zn1125.6 (2)N2—C13—C8115.9 (2)
C8—N1—Zn1113.17 (17)N2—C14—C15126.8 (3)
C14—N2—C13121.7 (2)N2—C14—H14A116.6
C14—N2—Zn1125.19 (19)C15—C14—H14A116.6
C13—N2—Zn1112.96 (17)C16—C15—C20118.0 (3)
O1—C1—C2118.8 (2)C16—C15—C14117.0 (3)
O1—C1—C6122.9 (3)C20—C15—C14125.0 (3)
C2—C1—C6118.3 (2)C17—C16—C15122.8 (3)
C3—C2—C1121.6 (3)C17—C16—H16A118.6
C3—C2—H2A119.2C15—C16—H16A118.6
C1—C2—H2A119.2C16—C17—C18118.6 (3)
O3—C3—C2123.4 (3)C16—C17—H17A120.7
O3—C3—C4116.5 (2)C18—C17—H17A120.7
C2—C3—C4120.1 (3)O4—C18—C19120.6 (3)
C5—C4—C3119.1 (3)O4—C18—C17118.9 (2)
C5—C4—H4A120.5C19—C18—C17120.4 (3)
C3—C4—H4A120.5C18—C19—C20121.8 (3)
C4—C5—C6122.8 (3)C18—C19—H19A119.1
C4—C5—H5A118.6C20—C19—H19A119.1
C6—C5—H5A118.6O2—C20—C19118.3 (2)
C5—C6—C1118.1 (3)O2—C20—C15123.4 (2)
C5—C6—C7116.6 (2)C19—C20—C15118.3 (2)
C1—C6—C7125.3 (3)Zn1—O1W—H2W1113.9
N1—C7—C6126.4 (3)Zn1—O1W—H1W1102.4
N1—C7—H7A116.8H2W1—O1W—H1W1107.7
C6—C7—H7A116.8H1W2—O2W—H2W2107.7
C9—C8—N1125.3 (3)H2W3—O3W—H1W3103.5
C9—C8—C13119.2 (3)H1W4—O4W—H2W4107.7
O2—Zn1—O1—C1169.1 (2)C5—C6—C7—N1178.5 (3)
O1W—Zn1—O1—C193.8 (3)C1—C6—C7—N11.6 (5)
N1—Zn1—O1—C17.6 (3)C7—N1—C8—C914.6 (4)
N2—Zn1—O1—C171.2 (3)Zn1—N1—C8—C9166.5 (2)
O1—Zn1—O2—C20146.0 (2)C7—N1—C8—C13164.6 (3)
O1W—Zn1—O2—C20116.5 (2)Zn1—N1—C8—C1314.4 (3)
N1—Zn1—O2—C2046.0 (4)N1—C8—C9—C10177.3 (3)
N2—Zn1—O2—C208.5 (2)C13—C8—C9—C101.8 (4)
O2—Zn1—N1—C7107.0 (3)C8—C9—C10—C111.8 (5)
O1—Zn1—N1—C76.4 (3)C9—C10—C11—C120.6 (5)
O1W—Zn1—N1—C790.7 (3)C10—C11—C12—C130.6 (5)
N2—Zn1—N1—C7163.0 (3)C11—C12—C13—N2179.5 (3)
O2—Zn1—N1—C871.9 (4)C11—C12—C13—C80.5 (4)
O1—Zn1—N1—C8172.57 (19)C14—N2—C13—C1216.6 (4)
O1W—Zn1—N1—C890.3 (2)Zn1—N2—C13—C12167.9 (2)
N2—Zn1—N1—C815.98 (19)C14—N2—C13—C8163.4 (3)
O2—Zn1—N2—C144.4 (2)Zn1—N2—C13—C812.1 (3)
O1—Zn1—N2—C1494.4 (3)C9—C8—C13—C120.7 (4)
O1W—Zn1—N2—C14101.3 (2)N1—C8—C13—C12178.5 (3)
N1—Zn1—N2—C14160.2 (3)C9—C8—C13—N2179.3 (3)
O2—Zn1—N2—C13179.72 (19)N1—C8—C13—N21.5 (4)
O1—Zn1—N2—C1380.9 (3)C13—N2—C14—C15175.9 (3)
O1W—Zn1—N2—C1383.36 (19)Zn1—N2—C14—C150.9 (4)
N1—Zn1—N2—C1315.15 (19)N2—C14—C15—C16177.1 (3)
Zn1—O1—C1—C2174.6 (2)N2—C14—C15—C201.2 (5)
Zn1—O1—C1—C65.5 (4)C20—C15—C16—C170.7 (5)
O1—C1—C2—C3179.6 (3)C14—C15—C16—C17177.8 (3)
C6—C1—C2—C30.4 (4)C15—C16—C17—C181.2 (5)
C1—C2—C3—O3179.7 (3)C16—C17—C18—O4179.3 (3)
C1—C2—C3—C40.2 (5)C16—C17—C18—C191.2 (5)
O3—C3—C4—C5179.7 (3)O4—C18—C19—C20179.9 (3)
C2—C3—C4—C50.2 (5)C17—C18—C19—C200.6 (5)
C3—C4—C5—C60.5 (5)Zn1—O2—C20—C19172.2 (2)
C4—C5—C6—C10.7 (5)Zn1—O2—C20—C159.0 (4)
C4—C5—C6—C7179.2 (3)C18—C19—C20—O2178.8 (3)
O1—C1—C6—C5179.4 (3)C18—C19—C20—C150.0 (4)
C2—C1—C6—C50.6 (4)C16—C15—C20—O2178.8 (3)
O1—C1—C6—C70.7 (5)C14—C15—C20—O22.9 (5)
C2—C1—C6—C7179.3 (3)C16—C15—C20—C190.0 (4)
C8—N1—C7—C6175.4 (3)C14—C15—C20—C19178.3 (3)
Zn1—N1—C7—C63.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O3Wi0.821.872.688 (3)175
O4—H4B···O4ii0.821.932.728 (3)164
O1W—H1W1···O2iii0.852.142.879 (3)146
O2W—H1W2···O10.852.313.066 (3)149
O2W—H1W2···O1W0.852.362.936 (3)125
O3W—H1W3···O4Wiv0.85 (2)1.95 (2)2.788 (3)169 (3)
O4W—H1W4···O4v0.851.872.685 (3)161
O1W—H2W1···O1iii0.851.912.670 (3)148
O2W—H2W2···O2Wvi0.852.422.732 (4)103
O3W—H2W3···O2W0.851.852.701 (3)173
O4W—H2W4···O20.851.992.774 (3)153
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+2, z+1; (iii) x1, y, z; (iv) x+1, y+1, z+1; (v) x+1, y+2, z+1; (vi) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Zn(C20H14N2O4)(H2O)]·3H2O
Mr483.77
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)4.7462 (1), 13.9290 (2), 15.1128 (2)
α, β, γ (°)82.147 (1), 82.367 (1), 85.640 (1)
V3)979.26 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.31
Crystal size (mm)0.45 × 0.44 × 0.06
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.591, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections
13930, 3830, 3151
Rint0.042
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.088, 1.03
No. of reflections3830
No. of parameters283
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.49

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O3Wi0.821.87002.688 (3)175
O4—H4B···O4ii0.821.93162.728 (3)164
O1W—H1W1···O2iii0.852.13722.879 (3)146
O2W—H1W2···O10.852.30683.066 (3)149
O2W—H1W2···O1W0.852.36442.936 (3)125
O3W—H1W3···O4Wiv0.85 (2)1.95 (2)2.788 (3)169 (3)
O4W—H1W4···O4v0.851.86522.685 (3)161
O1W—H2W1···O1iii0.851.91172.670 (3)148
O2W—H2W2···O2Wvi0.852.41852.732 (4)103
O3W—H2W3···O2W0.851.85392.701 (3)173
O4W—H2W4···O20.851.99112.774 (3)153
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+2, z+1; (iii) x1, y, z; (iv) x+1, y+1, z+1; (v) x+1, y+2, z+1; (vi) x, y+1, z+1.
 

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