catena-Poly[[[(1,10-phenanthroline-κ2N,N′)zinc]-μ-pyridine-2,3-dicarboxyl­ato-κ4N,O2:O2′,O3] monohydrate]

Qin, Z.-H.; Lou, S.-F.; Wang, N.; Wang, F.-Y.

doi:10.1107/S1600536811020344

metal-organic compounds

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Volume 67| Part 7| July 2011| Page m864

doi:10.1107/S1600536811020344

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catena-Poly[[[(1,10-phenanthroline-κ²N,N′)zinc]-μ-pyridine-2,3-dicarboxylato-κ⁴N,O²:O^2′,O³] monohydrate]

Zhen-Hua Qin,^a ^* Shu-Fang Lou,^a Na Wang ^a and Fu-Yu Wang ^a

^aShangqiu Medical College, Shangqiu, Henan 476100, People's Republic of China
^*Correspondence e-mail: qinzhenhua1969@163.com

(Received 14 April 2011; accepted 27 May 2011; online 4 June 2011)

In the title complex, {[Zn(C₇H₃NO₄)(C₁₂H₈N₂)]·H₂O}_n, the Zn^II ion is in a distorted octahedral environment, defined by two N atoms from a chelating 1,10-phenanthroline (phen) ligand and one N atom and three O atoms from two pyridine-2,3-dicarboxylate (2,3-pydc) ligands. The bridging 2,3-pydc ligands connect the Zn^II ions into a chain extending along [010]. O—H⋯O hydrogen bonds between the uncoordinated water molecules and the uncoordinated carboxylate O atoms, as well as π–π interactions between the pyridine rings of the phen ligands [centroid–centroid distance = 3.557 (2) Å], are observed.

Related literature

For complexes based on pyridine-2,3-dicarboxylic acid, see: Du et al. (2008 ); Han et al. (2006 ); Li & Li (2004 ); Patrick et al. (2003 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For a related structure, see: Shit et al. (2008 ).

Experimental

Crystal data

[Zn(C₇H₃NO₄)(C₁₂H₈N₂)]·H₂O
M_r = 428.69
Orthorhombic, P b c a
a = 12.2099 (8) Å
b = 11.6922 (8) Å
c = 23.2513 (15) Å
V = 3319.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 1.52 mm⁻¹
T = 293 K
0.23 × 0.19 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.721, T_max = 0.839
30212 measured reflections
3802 independent reflections
3010 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.175
S = 1.06
3802 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −1.02 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.102 (2)
Zn1—O2ⁱ	2.110 (2)
Zn1—O4ⁱ	2.062 (2)
Zn1—N1	2.142 (3)
Zn1—N2	2.139 (3)
Zn1—N3	2.131 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3	0.85	2.22	3.022 (5)	157
O1W—H1WB⋯O3ⁱⁱ	0.85	2.42	3.215 (5)	157
Symmetry code: (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020344/hy2421sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020344/hy2421Isup2.hkl

checkCIF report

Comment top

Pyridine-carboxylic acids are widely used to form supramolecular architectures due to their diverse coordination modes such as monodentate terminal, monodentate bridging and bidentate chelating. Recently, pyridine-2,3-dicarboxylic acid (2,3-H₂pydc) acts as a bidentate and bridging ligand to construct one-dimensional chain, two-dimensional layer and three-dimensional structures (Du et al., 2008; Han et al., 2006; Li & Li, 2004; Patrick et al., 2003). Herein, a one-dimensional polymeric complex based on 2,3-pydc was investigated.

The title compound is composed of polymeric chains and uncoordinated water molecules. The asymmetric unit contains one Zn^II ion, one uncoordinated water molecule, one 2,3-pydc ligand and one 1,10-phenanthroline (1,10-phen) ligand. The coordination geometry of the Zn^II ion can be described as distorted octahedral, which is defined by three N and three O atoms from one 1,10-phen and two 2,3-pydc ligands, with Zn—N and Zn—O distances of 2.131 (3)–2.142 (3) and 2.062 (2)–2.110 (2) Å, respectively (Fig. 1, Table 1). As shown in Fig. 2, adjacent Zn^II ions are bridged by 2,3-pydc ligands, which adopt a syn–anti configuration, with an internuclear Zn···Zn distance of 5.9206 (6) Å, building an infinite one-dimensional architecture. The 1,10-phen molecule serves as a bidentate chelating ligand to coordinate to the Zn^II ion. In the chain, the dihedral angle between the adjacent 1,10-phen ligands is 65.24 (3)°.

According to the search results in CSD database (Conquest version 1.12) (Allen, 2002), an isomorphous complex {[Mn(C₇H₃NO₄)(C₁₂H₈N₂)].H₂O}_n is reported (Shit et al., 2008).

Related literature top

For complexes based on pyridine-2,3-dicarboxylic acid, see: Du et al. (2008); Han et al. (2006); Li & Li (2004); Patrick et al. (2003). For a description of the Cambridge Structural Database, see: Allen (2002). For a related structure, see: Shit et al. (2008).

Experimental top

A mixture of pyridine-2,3-dicarboxylic acid (0.2 mmol), Zn(CH₃COOH)₂.2H₂O (0.2 mmol), 1,10-phenanthroline (0.1 mmol) and 10 ml me thanol/distilled water(v/v 9:2) sealed in a 25 ml Teflon-lined stainless steel autoclave was kept at 393 K for three days and then cooled to room temperature. Colorless crystals suitable for X-ray analysis were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Part of the chain structure in the title complex. Displacement ellipsoids are drawn at the 30% probability level. Uncoordinated water molecule has been omitted. [Symmetry code: (i) 1/2 - x, -1/2 + y, z.]
	Fig. 2. The packing diagram of the title complex. Dashed lines denote hydrogen bonds. H atoms not involving in hydrogen bonds have been omitted.

catena-Poly[[[(1,10-phenanthroline-κ²N,N')zinc]- µ-pyridine-2,3-dicarboxylato- κ⁴N,O²:O^2',O³] monohydrate] top

Crystal data top

[Zn(C₇H₃NO₄)(C₁₂H₈N₂)]·H₂O	F(000) = 1744
M_r = 428.69	D_x = 1.716 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4015 reflections
a = 12.2099 (8) Å	θ = 1.8–28.3°
b = 11.6922 (8) Å	µ = 1.52 mm⁻¹
c = 23.2513 (15) Å	T = 293 K
V = 3319.4 (4) Å³	Block, colorless
Z = 8	0.23 × 0.19 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	3802 independent reflections
Radiation source: fine-focus sealed tube	3010 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.721, T_max = 0.839	k = −15→15
30212 measured reflections	l = −29→29

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1103P)² + 4.4449P] where P = (F_o² + 2F_c²)/3
3802 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −1.02 e Å⁻³

Crystal data top

[Zn(C₇H₃NO₄)(C₁₂H₈N₂)]·H₂O	V = 3319.4 (4) Å³
M_r = 428.69	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.2099 (8) Å	µ = 1.52 mm⁻¹
b = 11.6922 (8) Å	T = 293 K
c = 23.2513 (15) Å	0.23 × 0.19 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	3802 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3010 reflections with I > 2σ(I)
T_min = 0.721, T_max = 0.839	R_int = 0.040
30212 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.06	Δρ_max = 0.76 e Å⁻³
3802 reflections	Δρ_min = −1.02 e Å⁻³
253 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.21166 (4)	0.05837 (3)	0.378838 (18)	0.02796 (19)
O1	0.1506 (2)	0.22624 (19)	0.37472 (10)	0.0250 (5)
O2	0.19575 (19)	0.4075 (2)	0.38954 (11)	0.0248 (5)
O3	0.2708 (3)	0.4531 (3)	0.53194 (15)	0.0586 (10)
O4	0.3580 (2)	0.53247 (19)	0.45856 (10)	0.0288 (5)
N1	0.0847 (2)	−0.0270 (2)	0.33197 (12)	0.0230 (6)
N2	0.2625 (2)	0.0835 (2)	0.29172 (12)	0.0242 (6)
N3	0.3382 (2)	0.1532 (2)	0.42019 (11)	0.0217 (5)
C1	−0.0016 (3)	−0.0834 (3)	0.35158 (15)	0.0286 (7)
H1A	−0.0132	−0.0853	0.3911	0.034*
C2	−0.0768 (3)	−0.1405 (3)	0.31582 (17)	0.0345 (8)
H2A	−0.1351	−0.1809	0.3317	0.041*
C3	−0.0631 (3)	−0.1360 (3)	0.25741 (17)	0.0326 (8)
H3A	−0.1124	−0.1727	0.2332	0.039*
C4	0.0263 (3)	−0.0752 (3)	0.23440 (16)	0.0277 (7)
C5	0.0465 (3)	−0.0641 (3)	0.17420 (17)	0.0368 (9)
H5A	−0.0009	−0.0988	0.1483	0.044*
C6	0.1321 (3)	−0.0049 (4)	0.15423 (15)	0.0384 (9)
H6A	0.1427	0.0009	0.1147	0.046*
C7	0.2082 (3)	0.0498 (3)	0.19250 (16)	0.0288 (8)
C8	0.3005 (3)	0.1110 (3)	0.17423 (17)	0.0342 (8)
H8A	0.3138	0.1208	0.1352	0.041*
C9	0.3705 (3)	0.1557 (3)	0.21347 (16)	0.0349 (8)
H9A	0.4322	0.1958	0.2015	0.042*
C10	0.3491 (3)	0.1410 (3)	0.27237 (16)	0.0307 (8)
H10A	0.3973	0.1726	0.2989	0.037*
C11	0.1920 (3)	0.0382 (3)	0.25240 (15)	0.0231 (7)
C12	0.0994 (3)	−0.0230 (3)	0.27382 (14)	0.0225 (6)
C13	0.3092 (2)	0.2624 (3)	0.43099 (13)	0.0187 (6)
C14	0.3641 (3)	0.3299 (3)	0.47056 (14)	0.0219 (6)
C15	0.4553 (3)	0.2838 (3)	0.49769 (16)	0.0327 (8)
H15A	0.4938	0.3266	0.5247	0.039*
C16	0.4885 (3)	0.1736 (3)	0.48438 (18)	0.0379 (9)
H16A	0.5515	0.1428	0.5008	0.045*
C17	0.4264 (3)	0.1104 (3)	0.44629 (16)	0.0306 (8)
H17A	0.4467	0.0353	0.4386	0.037*
C18	0.3260 (3)	0.4482 (3)	0.48823 (15)	0.0268 (7)
C19	0.2113 (2)	0.3025 (3)	0.39622 (14)	0.0184 (6)
O1W	0.2841 (4)	0.6974 (4)	0.57381 (19)	0.0825 (14)
H1WA	0.2747	0.6382	0.5532	0.124*
H1WB	0.2737	0.7562	0.5531	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0332 (3)	0.0191 (3)	0.0316 (3)	−0.00121 (15)	−0.00367 (16)	−0.00071 (14)
O1	0.0252 (12)	0.0133 (11)	0.0364 (13)	−0.0015 (9)	−0.0122 (10)	−0.0010 (9)
O2	0.0259 (12)	0.0095 (11)	0.0390 (13)	0.0011 (9)	−0.0060 (10)	−0.0012 (9)
O3	0.089 (3)	0.049 (2)	0.0371 (18)	0.0081 (17)	0.0260 (17)	−0.0036 (14)
O4	0.0411 (14)	0.0166 (11)	0.0286 (12)	−0.0053 (10)	−0.0077 (10)	−0.0003 (9)
N1	0.0236 (14)	0.0206 (13)	0.0247 (13)	−0.0018 (11)	−0.0032 (11)	0.0009 (11)
N2	0.0279 (14)	0.0189 (13)	0.0257 (14)	−0.0032 (11)	−0.0027 (11)	0.0006 (11)
N3	0.0252 (14)	0.0138 (12)	0.0260 (13)	−0.0005 (10)	−0.0049 (11)	0.0020 (10)
C1	0.0278 (17)	0.0292 (18)	0.0288 (18)	−0.0025 (14)	−0.0008 (14)	0.0031 (14)
C2	0.0253 (17)	0.0304 (19)	0.048 (2)	−0.0060 (14)	−0.0013 (16)	0.0016 (16)
C3	0.0268 (17)	0.0309 (19)	0.040 (2)	−0.0039 (15)	−0.0074 (15)	−0.0068 (15)
C4	0.0266 (17)	0.0252 (17)	0.0314 (18)	0.0019 (13)	−0.0067 (14)	−0.0047 (13)
C5	0.037 (2)	0.046 (2)	0.0278 (18)	0.0025 (17)	−0.0112 (16)	−0.0066 (15)
C6	0.043 (2)	0.051 (2)	0.0213 (17)	0.0007 (18)	−0.0068 (15)	−0.0019 (16)
C7	0.0320 (19)	0.031 (2)	0.0229 (17)	0.0047 (14)	−0.0040 (13)	0.0016 (13)
C8	0.043 (2)	0.033 (2)	0.0273 (18)	0.0008 (16)	0.0061 (15)	0.0068 (15)
C9	0.039 (2)	0.0272 (18)	0.039 (2)	−0.0074 (15)	0.0070 (16)	0.0053 (15)
C10	0.0335 (18)	0.0228 (17)	0.0358 (19)	−0.0083 (14)	−0.0003 (15)	0.0011 (14)
C11	0.0262 (16)	0.0192 (15)	0.0238 (16)	0.0014 (12)	−0.0047 (13)	0.0005 (12)
C12	0.0229 (16)	0.0193 (15)	0.0253 (16)	0.0003 (12)	−0.0051 (12)	0.0002 (12)
C13	0.0217 (14)	0.0157 (14)	0.0188 (14)	−0.0006 (11)	−0.0015 (11)	0.0016 (11)
C14	0.0279 (16)	0.0152 (14)	0.0227 (15)	−0.0050 (12)	−0.0033 (12)	0.0014 (11)
C15	0.036 (2)	0.0255 (18)	0.0363 (19)	−0.0051 (14)	−0.0167 (16)	0.0013 (14)
C16	0.034 (2)	0.0265 (19)	0.053 (2)	0.0010 (15)	−0.0228 (18)	0.0048 (16)
C17	0.0296 (18)	0.0182 (16)	0.044 (2)	0.0040 (13)	−0.0109 (15)	0.0016 (14)
C18	0.0351 (19)	0.0217 (17)	0.0237 (16)	−0.0009 (13)	−0.0046 (14)	−0.0049 (12)
C19	0.0218 (15)	0.0156 (14)	0.0178 (14)	0.0004 (11)	−0.0007 (11)	−0.0003 (11)
O1W	0.121 (4)	0.069 (3)	0.057 (3)	0.019 (2)	−0.026 (2)	−0.006 (2)

Geometric parameters (Å, º) top

Zn1—O1	2.102 (2)	C5—C6	1.336 (6)
Zn1—O2ⁱ	2.110 (2)	C5—H5A	0.9300
Zn1—O4ⁱ	2.062 (2)	C6—C7	1.436 (5)
Zn1—N1	2.142 (3)	C6—H6A	0.9300
Zn1—N2	2.139 (3)	C7—C8	1.401 (5)
Zn1—N3	2.131 (3)	C7—C11	1.413 (5)
O1—C19	1.262 (4)	C8—C9	1.355 (6)
O2—C19	1.252 (4)	C8—H8A	0.9300
O3—C18	1.221 (5)	C9—C10	1.405 (5)
O4—C18	1.265 (4)	C9—H9A	0.9300
N1—C1	1.324 (4)	C10—H10A	0.9300
N1—C12	1.365 (4)	C11—C12	1.429 (5)
N2—C10	1.331 (5)	C13—C14	1.386 (4)
N2—C11	1.362 (4)	C13—C19	1.518 (4)
N3—C17	1.333 (4)	C14—C15	1.389 (5)
N3—C13	1.349 (4)	C14—C18	1.516 (4)
C1—C2	1.407 (5)	C15—C16	1.386 (5)
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.369 (6)	C16—C17	1.381 (5)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.408 (5)	C17—H17A	0.9300
C3—H3A	0.9300	O1W—H1WA	0.85
C4—C12	1.417 (5)	O1W—H1WB	0.85
C4—C5	1.427 (5)

O4ⁱ—Zn1—O1	91.81 (9)	C5—C6—H6A	119.3
O4ⁱ—Zn1—O2ⁱ	89.56 (9)	C7—C6—H6A	119.3
O1—Zn1—O2ⁱ	167.49 (9)	C8—C7—C11	117.4 (3)
O4ⁱ—Zn1—N3	88.28 (10)	C8—C7—C6	124.0 (4)
O1—Zn1—N3	78.00 (9)	C11—C7—C6	118.6 (3)
O2ⁱ—Zn1—N3	89.61 (10)	C9—C8—C7	120.0 (3)
O4ⁱ—Zn1—N2	172.42 (11)	C9—C8—H8A	120.0
O1—Zn1—N2	86.07 (10)	C7—C8—H8A	120.0
O2ⁱ—Zn1—N2	94.09 (11)	C8—C9—C10	119.4 (3)
N3—Zn1—N2	98.36 (11)	C8—C9—H9A	120.3
O4ⁱ—Zn1—N1	95.17 (11)	C10—C9—H9A	120.3
O1—Zn1—N1	98.93 (10)	N2—C10—C9	122.6 (3)
O2ⁱ—Zn1—N1	93.33 (10)	N2—C10—H10A	118.7
N3—Zn1—N1	175.47 (10)	C9—C10—H10A	118.7
N2—Zn1—N1	78.01 (11)	N2—C11—C7	122.4 (3)
C19—O1—Zn1	115.6 (2)	N2—C11—C12	117.5 (3)
C19—O2—Zn1ⁱⁱ	138.9 (2)	C7—C11—C12	120.1 (3)
C18—O4—Zn1ⁱⁱ	118.5 (2)	N1—C12—C4	122.9 (3)
C1—N1—C12	117.6 (3)	N1—C12—C11	117.8 (3)
C1—N1—Zn1	129.3 (2)	C4—C12—C11	119.3 (3)
C12—N1—Zn1	113.1 (2)	N3—C13—C14	122.4 (3)
C10—N2—C11	118.1 (3)	N3—C13—C19	113.6 (3)
C10—N2—Zn1	128.3 (2)	C14—C13—C19	124.0 (3)
C11—N2—Zn1	113.5 (2)	C13—C14—C15	117.9 (3)
C17—N3—C13	118.8 (3)	C13—C14—C18	123.5 (3)
C17—N3—Zn1	126.6 (2)	C15—C14—C18	118.5 (3)
C13—N3—Zn1	112.7 (2)	C16—C15—C14	119.7 (3)
N1—C1—C2	123.5 (3)	C16—C15—H15A	120.2
N1—C1—H1A	118.3	C14—C15—H15A	120.2
C2—C1—H1A	118.3	C17—C16—C15	118.7 (3)
C3—C2—C1	119.2 (3)	C17—C16—H16A	120.7
C3—C2—H2A	120.4	C15—C16—H16A	120.7
C1—C2—H2A	120.4	N3—C17—C16	122.4 (3)
C2—C3—C4	119.4 (3)	N3—C17—H17A	118.8
C2—C3—H3A	120.3	C16—C17—H17A	118.8
C4—C3—H3A	120.3	O3—C18—O4	126.0 (3)
C3—C4—C12	117.4 (3)	O3—C18—C14	116.0 (3)
C3—C4—C5	123.6 (3)	O4—C18—C14	117.9 (3)
C12—C4—C5	119.1 (3)	O2—C19—O1	123.7 (3)
C6—C5—C4	121.6 (3)	O2—C19—C13	119.2 (3)
C6—C5—H5A	119.2	O1—C19—C13	117.1 (3)
C4—C5—H5A	119.2	H1WA—O1W—H1WB	108.7
C5—C6—C7	121.4 (3)

O4ⁱ—Zn1—O1—C19	88.5 (2)	Zn1—N2—C11—C7	177.2 (3)
O2ⁱ—Zn1—O1—C19	−7.6 (6)	C10—N2—C11—C12	−179.9 (3)
N3—Zn1—O1—C19	0.6 (2)	Zn1—N2—C11—C12	−2.9 (4)
N2—Zn1—O1—C19	−98.8 (2)	C8—C7—C11—N2	−0.2 (5)
N1—Zn1—O1—C19	−176.0 (2)	C6—C7—C11—N2	177.4 (3)
O4ⁱ—Zn1—N1—C1	−4.8 (3)	C8—C7—C11—C12	179.9 (3)
O1—Zn1—N1—C1	−97.5 (3)	C6—C7—C11—C12	−2.4 (5)
O2ⁱ—Zn1—N1—C1	85.0 (3)	C1—N1—C12—C4	0.6 (5)
N2—Zn1—N1—C1	178.5 (3)	Zn1—N1—C12—C4	179.1 (3)
O4ⁱ—Zn1—N1—C12	176.9 (2)	C1—N1—C12—C11	179.6 (3)
O1—Zn1—N1—C12	84.2 (2)	Zn1—N1—C12—C11	−1.9 (4)
O2ⁱ—Zn1—N1—C12	−93.3 (2)	C3—C4—C12—N1	−1.8 (5)
N2—Zn1—N1—C12	0.2 (2)	C5—C4—C12—N1	178.4 (3)
O1—Zn1—N2—C10	78.1 (3)	C3—C4—C12—C11	179.2 (3)
O2ⁱ—Zn1—N2—C10	−89.4 (3)	C5—C4—C12—C11	−0.7 (5)
N3—Zn1—N2—C10	0.8 (3)	N2—C11—C12—N1	3.3 (4)
N1—Zn1—N2—C10	178.1 (3)	C7—C11—C12—N1	−176.9 (3)
O1—Zn1—N2—C11	−98.5 (2)	N2—C11—C12—C4	−177.7 (3)
O2ⁱ—Zn1—N2—C11	94.0 (2)	C7—C11—C12—C4	2.2 (5)
N3—Zn1—N2—C11	−175.8 (2)	C17—N3—C13—C14	−3.6 (5)
N1—Zn1—N2—C11	1.5 (2)	Zn1—N3—C13—C14	161.9 (2)
O4ⁱ—Zn1—N3—C17	81.9 (3)	C17—N3—C13—C19	176.9 (3)
O1—Zn1—N3—C17	174.1 (3)	Zn1—N3—C13—C19	−17.7 (3)
O2ⁱ—Zn1—N3—C17	−7.7 (3)	N3—C13—C14—C15	3.1 (5)
N2—Zn1—N3—C17	−101.8 (3)	C19—C13—C14—C15	−177.4 (3)
O4ⁱ—Zn1—N3—C13	−82.2 (2)	N3—C13—C14—C18	−173.2 (3)
O1—Zn1—N3—C13	10.0 (2)	C19—C13—C14—C18	6.3 (5)
O2ⁱ—Zn1—N3—C13	−171.8 (2)	C13—C14—C15—C16	0.4 (5)
N2—Zn1—N3—C13	94.2 (2)	C18—C14—C15—C16	176.8 (4)
C12—N1—C1—C2	1.3 (5)	C14—C15—C16—C17	−3.1 (6)
Zn1—N1—C1—C2	−176.9 (3)	C13—N3—C17—C16	0.6 (5)
N1—C1—C2—C3	−1.9 (6)	Zn1—N3—C17—C16	−162.6 (3)
C1—C2—C3—C4	0.5 (6)	C15—C16—C17—N3	2.7 (6)
C2—C3—C4—C12	1.2 (5)	Zn1ⁱⁱ—O4—C18—O3	−109.1 (4)
C2—C3—C4—C5	−179.0 (4)	Zn1ⁱⁱ—O4—C18—C14	74.6 (4)
C3—C4—C5—C6	179.6 (4)	C13—C14—C18—O3	95.4 (5)
C12—C4—C5—C6	−0.6 (6)	C15—C14—C18—O3	−80.8 (5)
C4—C5—C6—C7	0.3 (6)	C13—C14—C18—O4	−87.9 (4)
C5—C6—C7—C8	178.7 (4)	C15—C14—C18—O4	95.8 (4)
C5—C6—C7—C11	1.2 (6)	Zn1ⁱⁱ—O2—C19—O1	−143.6 (3)
C11—C7—C8—C9	0.4 (5)	Zn1ⁱⁱ—O2—C19—C13	35.2 (5)
C6—C7—C8—C9	−177.1 (4)	Zn1—O1—C19—O2	168.5 (3)
C7—C8—C9—C10	−0.5 (6)	Zn1—O1—C19—C13	−10.3 (4)
C11—N2—C10—C9	−0.4 (5)	N3—C13—C19—O2	−159.6 (3)
Zn1—N2—C10—C9	−176.9 (3)	C14—C13—C19—O2	20.9 (5)
C8—C9—C10—N2	0.5 (6)	N3—C13—C19—O1	19.2 (4)
C10—N2—C11—C7	0.3 (5)	C14—C13—C19—O1	−160.3 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3	0.85	2.22	3.022 (5)	157
O1W—H1WB···O3ⁱⁱ	0.85	2.42	3.215 (5)	157

Symmetry code: (ii) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₃NO₄)(C₁₂H₈N₂)]·H₂O
M_r	428.69
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	12.2099 (8), 11.6922 (8), 23.2513 (15)
V (Å³)	3319.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.52
Crystal size (mm)	0.23 × 0.19 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.721, 0.839
No. of measured, independent and observed [I > 2σ(I)] reflections	30212, 3802, 3010
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.175, 1.06
No. of reflections	3802
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −1.02

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O1	2.102 (2)	Zn1—N1	2.142 (3)
Zn1—O2ⁱ	2.110 (2)	Zn1—N2	2.139 (3)
Zn1—O4ⁱ	2.062 (2)	Zn1—N3	2.131 (3)

Symmetry code: (i) −x+1/2, y−1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3	0.85	2.22	3.022 (5)	157
O1W—H1WB···O3ⁱⁱ	0.85	2.42	3.215 (5)	157

Symmetry code: (ii) −x+1/2, y+1/2, z.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Du, L., Fang, R.-B. & Zhao, Q.-H. (2008). Chin. J. Chem. 26, 957–961. CrossRef CAS Google Scholar
Han, Z.-B., Ma, Y., Sun, Z.-G. & Yu, W.-S. (2006). Inorg. Chem. Commun. 9, 844–847. CrossRef CAS Google Scholar
Li, L. & Li, Y. (2004). J. Mol. Struct. 694, 199–203. CrossRef CAS Google Scholar
Patrick, B. O., Stevens, C. L., Storr, A. & Thompason, R. C. (2003). Polyhedron, 22, 3025–3035. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shit, S., Charkraborty, J., Howard, J. A. K., Spencer, E. C., Desplanches, C. & Mitra, S. (2008). Struct. Chem. 19, 553–558. CrossRef CAS Google Scholar

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Volume 67| Part 7| July 2011| Page m864

doi:10.1107/S1600536811020344

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