Aqua­bis­(5-butyl­pyridine-2-carboxyl­ato)zinc monohydrate

Tao, Y.-W.; Wang, Y.

doi:10.1107/S1600536811021623

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m908

doi:10.1107/S1600536811021623

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Aquabis(5-butylpyridine-2-carboxylato)zinc monohydrate

Yi-Wen Tao ^a and Yun Wang ^b ^*

^aSchool of Basic Science, Guangzhou Medical College, Guangzhou 510182, People's Republic of China, and ^bGuangdong Institute for Drug Control, Guangzhou 510180, People's Republic of China
^*Correspondence e-mail: yywentao@yahoo.com.cn

(Received 26 May 2011; accepted 5 June 2011; online 11 June 2011)

In the title complex, [Zn(C₁₀H₁₂NO₂)₂(H₂O)]·H₂O, the Zn^II ion is coordinated by two N and two O atoms from two 5-n-butylpyridine-2-carboxylato ligands and one O atom from a water molecule in a distorted square-pyramidal geometry. In the crystal, intermolecular O—H⋯O hydrogen bonds link molecules into a two-dimensional supramolecular structure parallel to (001).

Related literature

For related structures, see: Pons et al. (2004 ); Yoshikawa et al. (2002 ); Qin et al. (2007 ); He et al. (2007 ).

Experimental

Crystal data

[Zn(C₂₀H₁₂NO₂)₂(H₂O)]·H₂O
M_r = 457.81
Triclinic, $[P \overline 1]$
a = 9.6949 (13) Å
b = 10.0054 (14) Å
c = 11.9249 (17) Å
α = 97.799 (2)°
β = 91.533 (2)°
γ = 113.464 (2)°
V = 1047.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 293 K
0.48 × 0.42 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.594, T_max = 0.839
7770 measured reflections
3847 independent reflections
3410 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.075
S = 1.06
3847 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2B⋯O4	0.85	1.94	2.780 (2)	172
O2W—H2A⋯O4ⁱ	0.85	2.02	2.849 (2)	165
O1W—H1B⋯O2Wⁱⁱ	0.84	1.80	2.638 (2)	175
O1W—H1A⋯O2ⁱⁱⁱ	0.85	1.79	2.636 (2)	174
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z; (iii) -x+2, -y, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021623/hg5046sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021623/hg5046Isup2.hkl

checkCIF report

Comment top

As known for a long time, pyridine-2-carboxylato ion and its derivatives are good chelating ligands for many transition metals(Pons, et al., 2004; Yoshikawa, et al., 2002; Qin et al., 2007; He et al., 2007). Here, we report a new zinc complex based on 5-n-butylpyridine-2-carboxylate.

The crystal structure of the title compound,(I), is shown in Fig. 1. The coordination sphere of the Zn^II ion should be described as a distorted square-pyramidal, in which the four basal positions are occupied by two N atoms and two O atoms from two 5-n-butylpyridine-2-carboxylato ligands, and the fifth apical site is occupied by the O atom of the coordinated solvent water molecule. The Zn(II) ion is out of the plane formed by N₂O₂ unit 0.504 (8)Å towards the Zn—O_water bond. The average Zn—N, Zn—O_ligand, and the Zn—O_water are 2.094, 2.043, and 2.044Å, respectively, in agreement with the corresponding distances found in other Zn complexes containing similar ligands (Qin et al., 2007; He et al., 2007). It was noting that the title complex was linked into a two-dimensional supermolecular structure under the help of the intermolecular O—H···O hydrogen bonds interactions.

Related literature top

For related structures, see: Pons et al. (2004); Yoshikawa et al. (2002); Qin et al. (2007); He et al. (2007).

Experimental top

The title complex was prepared by the addition of a stiochiometric amount to zinc acetate dehydrate (0.054 mmol) to a hot aqueous solution (5 ml) of fusaric acid (30 mmol) which was extracted from the endophytic fungus phomopsis sp. from the mangrove tree on the South China Sea coast. The resulting solution was filtered, and colorless crystals were obtained by slow evaporation of a methanol-water solution (90:10 v/v) at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

Fig. 1. The molecular structure of the title complex with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Aquabis(5-butylpyridine-2-carboxylato)zinc monohydrate top

Crystal data top

[Zn(C₂₀H₁₂NO₂)₂(H₂O)]·H₂O	Z = 2
M_r = 457.81	F(000) = 480
Triclinic, P1	D_x = 1.452 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6949 (13) Å	Cell parameters from 5809 reflections
b = 10.0054 (14) Å	θ = 2.3–27.0°
c = 11.9249 (17) Å	µ = 1.21 mm⁻¹
α = 97.799 (2)°	T = 293 K
β = 91.533 (2)°	Prism, colorless
γ = 113.464 (2)°	0.48 × 0.42 × 0.15 mm
V = 1047.1 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3847 independent reflections
Radiation source: fine-focus sealed tube	3410 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
phi and ω scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −11→11
T_min = 0.594, T_max = 0.839	k = −12→12
7770 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0384P)² + 0.5567P] where P = (F_o² + 2F_c²)/3
3847 reflections	(Δ/σ)_max = 0.008
264 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Zn(C₂₀H₁₂NO₂)₂(H₂O)]·H₂O	γ = 113.464 (2)°
M_r = 457.81	V = 1047.1 (3) Å³
Triclinic, P1	Z = 2
a = 9.6949 (13) Å	Mo Kα radiation
b = 10.0054 (14) Å	µ = 1.21 mm⁻¹
c = 11.9249 (17) Å	T = 293 K
α = 97.799 (2)°	0.48 × 0.42 × 0.15 mm
β = 91.533 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3847 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	3410 reflections with I > 2σ(I)
T_min = 0.594, T_max = 0.839	R_int = 0.017
7770 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.06	Δρ_max = 0.47 e Å⁻³
3847 reflections	Δρ_min = −0.29 e Å⁻³
264 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.

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

	x	y	z	U_iso*/U_eq
C1	0.9784 (2)	0.0833 (2)	0.17910 (17)	0.0249 (4)
C2	1.0361 (2)	0.2469 (2)	0.22551 (17)	0.0239 (4)
C3	1.1290 (3)	0.3107 (2)	0.32451 (18)	0.0311 (5)
H3	1.1603	0.2528	0.3674	0.037*
C4	1.1761 (3)	0.4611 (2)	0.36059 (19)	0.0341 (5)
H4	1.2413	0.5071	0.4282	0.041*
C5	1.1283 (2)	0.5447 (2)	0.29835 (17)	0.0275 (4)
C6	1.0337 (2)	0.4707 (2)	0.19940 (17)	0.0250 (4)
H6	0.9991	0.5254	0.1555	0.030*
C7	1.1750 (3)	0.7081 (2)	0.33348 (18)	0.0336 (5)
H7A	1.1100	0.7396	0.2878	0.040*
H7B	1.2801	0.7601	0.3147	0.040*
C8	1.1666 (4)	0.7566 (3)	0.4578 (2)	0.0496 (7)
H8A	1.2515	0.7516	0.5025	0.059*
H8B	1.0716	0.6866	0.4823	0.059*
C9	1.1725 (4)	0.9123 (3)	0.4849 (2)	0.0544 (7)
H9A	1.0839	0.9153	0.4439	0.065*
H9B	1.1639	0.9341	0.5673	0.065*
C10	1.3102 (4)	1.0292 (3)	0.4550 (3)	0.0681 (9)
H10A	1.3987	1.0303	0.4976	0.102*
H10B	1.3044	1.1251	0.4743	0.102*
H10C	1.3193	1.0100	0.3734	0.102*
C11	0.6412 (2)	0.2796 (2)	−0.07353 (16)	0.0238 (4)
C12	0.5820 (2)	0.1149 (2)	−0.11734 (16)	0.0225 (4)
C13	0.4469 (2)	0.0367 (2)	−0.18239 (18)	0.0285 (5)
H13	0.3866	0.0852	−0.2049	0.034*
C14	0.4004 (2)	−0.1145 (2)	−0.21448 (18)	0.0303 (5)
H14	0.3074	−0.1704	−0.2593	0.036*
C15	0.4900 (3)	−0.1841 (2)	−0.18108 (17)	0.0281 (5)
C16	0.6254 (2)	−0.0962 (2)	−0.11735 (17)	0.0264 (4)
H16	0.6890	−0.1414	−0.0949	0.032*
C17	0.4419 (3)	−0.3486 (2)	−0.21017 (18)	0.0348 (5)
H17A	0.5116	−0.3770	−0.1667	0.042*
H17B	0.3397	−0.3986	−0.1853	0.042*
C18	0.4389 (4)	−0.4036 (3)	−0.3335 (2)	0.0471 (7)
H18A	0.5387	−0.3483	−0.3602	0.057*
H18B	0.3629	−0.3829	−0.3767	0.057*
C19	0.4019 (3)	−0.5685 (3)	−0.3597 (2)	0.0483 (7)
H19A	0.4110	−0.5946	−0.4414	0.058*
H19B	0.4777	−0.5890	−0.3161	0.058*
C20	0.2495 (4)	−0.6646 (3)	−0.3326 (3)	0.0684 (10)
H20A	0.2403	−0.6422	−0.2512	0.103*
H20B	0.2340	−0.7682	−0.3520	0.103*
H20C	0.1733	−0.6469	−0.3765	0.103*
N1	0.98977 (19)	0.32660 (18)	0.16371 (14)	0.0230 (4)
N2	0.67075 (19)	0.04994 (18)	−0.08590 (13)	0.0228 (3)
O1	0.88860 (16)	0.03799 (15)	0.09036 (12)	0.0277 (3)
O2	1.02181 (19)	0.00693 (17)	0.23255 (13)	0.0351 (4)
O3	0.76689 (16)	0.33710 (15)	−0.01438 (12)	0.0262 (3)
O4	0.56258 (16)	0.34586 (16)	−0.09763 (13)	0.0319 (3)
O1W	1.02425 (16)	0.24272 (15)	−0.09978 (12)	0.0253 (3)
H1A	1.0153	0.1655	−0.1447	0.038*
H1B	1.1118	0.2841	−0.0657	0.038*
O2W	0.69815 (17)	0.64141 (17)	0.00070 (14)	0.0364 (4)
H2A	0.6306	0.6516	0.0409	0.055*
H2B	0.6653	0.5519	−0.0315	0.055*
Zn1	0.86873 (3)	0.19830 (2)	0.010473 (19)	0.02289 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0274 (11)	0.0232 (10)	0.0270 (10)	0.0130 (9)	0.0052 (9)	0.0040 (8)
C2	0.0226 (10)	0.0245 (10)	0.0262 (10)	0.0113 (9)	0.0042 (8)	0.0036 (8)
C3	0.0358 (12)	0.0285 (11)	0.0303 (11)	0.0154 (10)	−0.0039 (9)	0.0032 (9)
C4	0.0394 (13)	0.0308 (12)	0.0278 (11)	0.0121 (10)	−0.0068 (10)	−0.0004 (9)
C5	0.0316 (11)	0.0231 (10)	0.0253 (10)	0.0090 (9)	0.0039 (9)	0.0015 (8)
C6	0.0281 (11)	0.0225 (10)	0.0252 (10)	0.0110 (9)	0.0035 (8)	0.0035 (8)
C7	0.0424 (13)	0.0221 (11)	0.0295 (11)	0.0072 (10)	−0.0006 (10)	0.0013 (9)
C8	0.085 (2)	0.0331 (13)	0.0338 (13)	0.0273 (14)	0.0130 (13)	0.0042 (10)
C9	0.085 (2)	0.0381 (15)	0.0421 (15)	0.0281 (15)	0.0152 (14)	0.0021 (11)
C10	0.073 (2)	0.0339 (15)	0.089 (2)	0.0174 (15)	0.0115 (18)	−0.0066 (15)
C11	0.0247 (10)	0.0241 (10)	0.0238 (10)	0.0115 (9)	0.0061 (8)	0.0019 (8)
C12	0.0224 (10)	0.0227 (10)	0.0220 (10)	0.0088 (8)	0.0053 (8)	0.0025 (8)
C13	0.0252 (11)	0.0319 (12)	0.0285 (11)	0.0128 (9)	0.0025 (9)	0.0013 (9)
C14	0.0246 (11)	0.0301 (11)	0.0272 (11)	0.0037 (9)	0.0008 (9)	−0.0017 (9)
C15	0.0349 (12)	0.0232 (10)	0.0208 (10)	0.0065 (9)	0.0046 (9)	0.0014 (8)
C16	0.0320 (11)	0.0230 (10)	0.0236 (10)	0.0105 (9)	0.0039 (9)	0.0039 (8)
C17	0.0450 (14)	0.0218 (11)	0.0283 (11)	0.0055 (10)	−0.0014 (10)	0.0005 (9)
C18	0.077 (2)	0.0301 (13)	0.0324 (13)	0.0203 (13)	0.0135 (12)	0.0027 (10)
C19	0.0670 (18)	0.0298 (13)	0.0418 (14)	0.0143 (13)	0.0186 (13)	−0.0012 (10)
C20	0.068 (2)	0.0414 (16)	0.069 (2)	0.0008 (15)	0.0174 (17)	−0.0152 (14)
N1	0.0237 (9)	0.0204 (8)	0.0241 (8)	0.0085 (7)	0.0012 (7)	0.0018 (7)
N2	0.0255 (9)	0.0207 (8)	0.0210 (8)	0.0085 (7)	0.0021 (7)	0.0018 (6)
O1	0.0304 (8)	0.0211 (7)	0.0310 (8)	0.0107 (6)	−0.0030 (6)	0.0020 (6)
O2	0.0506 (10)	0.0279 (8)	0.0316 (8)	0.0223 (8)	−0.0051 (7)	0.0020 (6)
O3	0.0234 (7)	0.0208 (7)	0.0327 (8)	0.0098 (6)	−0.0020 (6)	−0.0023 (6)
O4	0.0277 (8)	0.0270 (8)	0.0431 (9)	0.0161 (7)	−0.0029 (7)	−0.0016 (7)
O1W	0.0243 (7)	0.0229 (7)	0.0296 (7)	0.0116 (6)	0.0011 (6)	0.0012 (6)
O2W	0.0281 (8)	0.0241 (8)	0.0546 (10)	0.0112 (7)	−0.0004 (7)	−0.0025 (7)
Zn1	0.02298 (14)	0.01954 (13)	0.02499 (14)	0.00872 (10)	−0.00164 (9)	0.00013 (9)

Geometric parameters (Å, º) top

C1—O2	1.241 (2)	C13—C14	1.389 (3)
C1—O1	1.261 (3)	C13—H13	0.9500
C1—C2	1.519 (3)	C14—C15	1.391 (3)
C2—N1	1.345 (3)	C14—H14	0.9500
C2—C3	1.376 (3)	C15—C16	1.386 (3)
C3—C4	1.388 (3)	C15—C17	1.508 (3)
C3—H3	0.9500	C16—N2	1.342 (3)
C4—C5	1.387 (3)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.494 (3)
C5—C6	1.395 (3)	C17—H17A	0.9900
C5—C7	1.506 (3)	C17—H17B	0.9900
C6—N1	1.332 (3)	C18—C19	1.528 (3)
C6—H6	0.9500	C18—H18A	0.9900
C7—C8	1.511 (3)	C18—H18B	0.9900
C7—H7A	0.9900	C19—C20	1.480 (4)
C7—H7B	0.9900	C19—H19A	0.9900
C8—C9	1.525 (3)	C19—H19B	0.9900
C8—H8A	0.9900	C20—H20A	0.9800
C8—H8B	0.9900	C20—H20B	0.9800
C9—C10	1.474 (4)	C20—H20C	0.9800
C9—H9A	0.9900	N1—Zn1	2.1007 (16)
C9—H9B	0.9900	N2—Zn1	2.0877 (17)
C10—H10A	0.9800	O1—Zn1	2.0416 (14)
C10—H10B	0.9800	O3—Zn1	2.0443 (14)
C10—H10C	0.9800	O1W—Zn1	1.9825 (14)
C11—O4	1.243 (2)	O1W—H1A	0.8498
C11—O3	1.264 (2)	O1W—H1B	0.8440
C11—C12	1.521 (3)	O2W—H2A	0.8514
C12—N2	1.341 (3)	O2W—H2B	0.8510
C12—C13	1.377 (3)

O2—C1—O1	126.36 (19)	C15—C14—H14	120.0
O2—C1—C2	117.37 (18)	C16—C15—C14	117.25 (19)
O1—C1—C2	116.27 (17)	C16—C15—C17	120.7 (2)
N1—C2—C3	121.57 (19)	C14—C15—C17	122.0 (2)
N1—C2—C1	115.64 (17)	N2—C16—C15	122.97 (19)
C3—C2—C1	122.79 (18)	N2—C16—H16	118.5
C2—C3—C4	118.9 (2)	C15—C16—H16	118.5
C2—C3—H3	120.6	C18—C17—C15	114.50 (19)
C4—C3—H3	120.6	C18—C17—H17A	108.6
C5—C4—C3	120.3 (2)	C15—C17—H17A	108.6
C5—C4—H4	119.9	C18—C17—H17B	108.6
C3—C4—H4	119.9	C15—C17—H17B	108.6
C4—C5—C6	116.93 (19)	H17A—C17—H17B	107.6
C4—C5—C7	122.71 (19)	C17—C18—C19	113.5 (2)
C6—C5—C7	120.36 (19)	C17—C18—H18A	108.9
N1—C6—C5	122.96 (19)	C19—C18—H18A	108.9
N1—C6—H6	118.5	C17—C18—H18B	108.9
C5—C6—H6	118.5	C19—C18—H18B	108.9
C5—C7—C8	115.23 (19)	H18A—C18—H18B	107.7
C5—C7—H7A	108.5	C20—C19—C18	114.3 (2)
C8—C7—H7A	108.5	C20—C19—H19A	108.7
C5—C7—H7B	108.5	C18—C19—H19A	108.7
C8—C7—H7B	108.5	C20—C19—H19B	108.7
H7A—C7—H7B	107.5	C18—C19—H19B	108.7
C7—C8—C9	113.9 (2)	H19A—C19—H19B	107.6
C7—C8—H8A	108.8	C19—C20—H20A	109.5
C9—C8—H8A	108.8	C19—C20—H20B	109.5
C7—C8—H8B	108.8	H20A—C20—H20B	109.5
C9—C8—H8B	108.8	C19—C20—H20C	109.5
H8A—C8—H8B	107.7	H20A—C20—H20C	109.5
C10—C9—C8	114.8 (3)	H20B—C20—H20C	109.5
C10—C9—H9A	108.6	C6—N1—C2	119.38 (17)
C8—C9—H9A	108.6	C6—N1—Zn1	129.26 (14)
C10—C9—H9B	108.6	C2—N1—Zn1	111.10 (13)
C8—C9—H9B	108.6	C12—N2—C16	119.00 (17)
H9A—C9—H9B	107.6	C12—N2—Zn1	112.83 (13)
C9—C10—H10A	109.5	C16—N2—Zn1	128.17 (14)
C9—C10—H10B	109.5	C1—O1—Zn1	115.66 (13)
H10A—C10—H10B	109.5	C11—O3—Zn1	116.22 (12)
C9—C10—H10C	109.5	Zn1—O1W—H1A	111.6
H10A—C10—H10C	109.5	Zn1—O1W—H1B	110.8
H10B—C10—H10C	109.5	H1A—O1W—H1B	110.4
O4—C11—O3	125.56 (18)	H2A—O2W—H2B	108.2
O4—C11—C12	117.92 (17)	O1W—Zn1—O1	106.09 (6)
O3—C11—C12	116.52 (17)	O1W—Zn1—O3	102.80 (6)
N2—C12—C13	122.02 (18)	O1—Zn1—O3	151.11 (6)
N2—C12—C11	114.71 (17)	O1W—Zn1—N2	104.39 (6)
C13—C12—C11	123.26 (18)	O1—Zn1—N2	92.68 (6)
C12—C13—C14	118.69 (19)	O3—Zn1—N2	79.70 (6)
C12—C13—H13	120.7	O1W—Zn1—N1	103.25 (6)
C14—C13—H13	120.7	O1—Zn1—N1	79.91 (6)
C13—C14—C15	120.04 (19)	O3—Zn1—N1	93.96 (6)
C13—C14—H14	120.0	N2—Zn1—N1	152.36 (6)

O2—C1—C2—N1	178.32 (18)	C1—C2—N1—Zn1	−6.2 (2)
O1—C1—C2—N1	−2.8 (3)	C13—C12—N2—C16	−1.0 (3)
O2—C1—C2—C3	−2.0 (3)	C11—C12—N2—C16	177.81 (17)
O1—C1—C2—C3	176.9 (2)	C13—C12—N2—Zn1	179.31 (15)
N1—C2—C3—C4	−0.3 (3)	C11—C12—N2—Zn1	−1.9 (2)
C1—C2—C3—C4	−179.9 (2)	C15—C16—N2—C12	−0.2 (3)
C2—C3—C4—C5	0.8 (3)	C15—C16—N2—Zn1	179.46 (15)
C3—C4—C5—C6	−0.5 (3)	O2—C1—O1—Zn1	−170.40 (17)
C3—C4—C5—C7	179.7 (2)	C2—C1—O1—Zn1	10.8 (2)
C4—C5—C6—N1	−0.3 (3)	O4—C11—O3—Zn1	179.89 (16)
C7—C5—C6—N1	179.44 (19)	C12—C11—O3—Zn1	0.5 (2)
C4—C5—C7—C8	−45.1 (3)	C1—O1—Zn1—O1W	89.95 (15)
C6—C5—C7—C8	135.1 (2)	C1—O1—Zn1—O3	−90.86 (18)
C5—C7—C8—C9	−164.3 (2)	C1—O1—Zn1—N2	−164.24 (14)
C7—C8—C9—C10	−59.7 (4)	C1—O1—Zn1—N1	−11.06 (14)
O4—C11—C12—N2	−178.46 (18)	C11—O3—Zn1—O1W	101.39 (14)
O3—C11—C12—N2	0.9 (3)	C11—O3—Zn1—O1	−77.81 (18)
O4—C11—C12—C13	0.4 (3)	C11—O3—Zn1—N2	−1.18 (14)
O3—C11—C12—C13	179.76 (19)	C11—O3—Zn1—N1	−154.05 (14)
N2—C12—C13—C14	1.1 (3)	C12—N2—Zn1—O1W	−99.05 (13)
C11—C12—C13—C14	−177.59 (18)	C16—N2—Zn1—O1W	81.32 (17)
C12—C13—C14—C15	−0.1 (3)	C12—N2—Zn1—O1	153.59 (13)
C13—C14—C15—C16	−1.0 (3)	C16—N2—Zn1—O1	−26.04 (17)
C13—C14—C15—C17	177.75 (19)	C12—N2—Zn1—O3	1.66 (13)
C14—C15—C16—N2	1.1 (3)	C16—N2—Zn1—O3	−177.97 (17)
C17—C15—C16—N2	−177.61 (19)	C12—N2—Zn1—N1	80.37 (19)
C16—C15—C17—C18	−112.4 (3)	C16—N2—Zn1—N1	−99.3 (2)
C14—C15—C17—C18	68.9 (3)	C6—N1—Zn1—O1W	78.55 (18)
C15—C17—C18—C19	175.5 (2)	C2—N1—Zn1—O1W	−95.41 (14)
C17—C18—C19—C20	63.4 (4)	C6—N1—Zn1—O1	−177.13 (18)
C5—C6—N1—C2	0.9 (3)	C2—N1—Zn1—O1	8.90 (13)
C5—C6—N1—Zn1	−172.66 (15)	C6—N1—Zn1—O3	−25.60 (18)
C3—C2—N1—C6	−0.6 (3)	C2—N1—Zn1—O3	160.44 (13)
C1—C2—N1—C6	179.13 (17)	C6—N1—Zn1—N2	−100.9 (2)
C3—C2—N1—Zn1	174.08 (16)	C2—N1—Zn1—N2	85.17 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2B···O4	0.85	1.94	2.780 (2)	172
O2W—H2A···O4ⁱ	0.85	2.02	2.849 (2)	165
O1W—H1B···O2Wⁱⁱ	0.84	1.80	2.638 (2)	175
O1W—H1A···O2ⁱⁱⁱ	0.85	1.79	2.636 (2)	174

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

Experimental details

Crystal data
Chemical formula	[Zn(C₂₀H₁₂NO₂)₂(H₂O)]·H₂O
M_r	457.81
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.6949 (13), 10.0054 (14), 11.9249 (17)
α, β, γ (°)	97.799 (2), 91.533 (2), 113.464 (2)
V (Å³)	1047.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.48 × 0.42 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.594, 0.839
No. of measured, independent and observed [I > 2σ(I)] reflections	7770, 3847, 3410
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.075, 1.06
No. of reflections	3847
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.29

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2B···O4	0.85	1.94	2.780 (2)	172
O2W—H2A···O4ⁱ	0.85	2.02	2.849 (2)	165
O1W—H1B···O2Wⁱⁱ	0.84	1.80	2.638 (2)	175
O1W—H1A···O2ⁱⁱⁱ	0.85	1.79	2.636 (2)	174

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

Acknowledgements

This work was supported by the Guangzhou Science and Technology Projects Fund (2010Y1-C371), the Guangzhou Municipal Bureau of Education Projects Fund (10 A168) and the doctoral startup fund of Guangzhou Medical College (2008 C25).

References

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