catena-Poly[[aqua­(dipyrido[3,2-a:2′,3′-c]phenazine-κ2N4,N5)zinc(II)]-μ-pyrazine-2,3-dicarboxyl­ato-κ3N1,O2:O3]

Wang, X.; Li, X.-Y.; Wang, Q.-W.; Che, G.-B.

doi:10.1107/S1600536808022824

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1078-m1079

doi:10.1107/S1600536808022824

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catena-Poly[[aqua(dipyrido[3,2-a:2′,3′-c]phenazine-κ²N⁴,N⁵)zinc(II)]-μ-pyrazine-2,3-dicarboxylato-κ³N¹,O²:O³]

Xin Wang,^a Xiu-Ying Li,^b Qing-Wei Wang ^b and Guang-Bo Che ^b ^*

^aJilin Agriculture Engineering Polytechnic College, Siping 136000, People's Republic of China, and ^bDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
^*Correspondence e-mail: guangbochejl@yahoo.com

(Received 9 July 2008; accepted 21 July 2008; online 26 July 2008)

In the title compound, [Zn(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]_n or [Zn(PZDC)(DPPZ)(H₂O)]_n (where DPPZ is dipyrido[3,2-a:2′,3′-c]phenazine and H₂PZDC is pyrazine-2,3-dicarboxylic acid), the Zn atom is six-coordinated in a slightly distorted octahedral coordination geometry by three N atoms from one DPPZ ligand and one PZDC²⁻ dianion, three O atoms from two different PZDC²⁻ ligands and one water molecule. Each PZDC²⁻ dianion serves as a spacer, connecting adjacent metal atoms into a polymeric chain structure parallel to the b axis. The chain motif is consolidated into a three-dimensional supramolecular network by O—H⋯O and O—H⋯N hydrogen bonds and π–π aromatic stacking interactions involving adjacent DPPZ ligands and PZDC²⁻ dianions with centroid–centroid separations of 3.522 (6) and 3.732 (8) Å, respectively.

Related literature

For related literature, see: Che et al. (2008 ); Che, Li et al. (2006 ); Che, Xu & Liu (2006 ); Liu et al. (2008 ); Xu et al. (2008 ).

Experimental

Crystal data

[Zn(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]
M_r = 531.78
Triclinic, $[P \overline 1]$
a = 6.7821 (14) Å
b = 7.4349 (15) Å
c = 20.410 (4) Å
α = 91.26 (3)°
β = 95.77 (3)°
γ = 98.16 (3)°
V = 1012.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.27 mm⁻¹
T = 292 (2) K
0.31 × 0.29 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.681, T_max = 0.765
9890 measured reflections
4412 independent reflections
3278 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.148
S = 1.07
4412 reflections
333 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—Zn	2.130 (3)
N2—Zn	2.167 (3)
N5—Zn	2.147 (3)
O1—Zn	2.172 (3)
O1W—Zn	2.120 (3)
O4—Znⁱ	2.051 (3)

O4ⁱⁱ—Zn—O1W	90.19 (13)
O4ⁱⁱ—Zn—N1	90.37 (12)
O1W—Zn—N1	96.93 (13)
O4ⁱⁱ—Zn—N5	97.78 (12)
O1W—Zn—N5	86.87 (13)
N1—Zn—N5	171.02 (11)
O4ⁱⁱ—Zn—N2	98.61 (11)
O1W—Zn—N2	169.43 (13)
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—HW1A⋯O3ⁱⁱⁱ	0.66 (5)	2.01 (5)	2.662 (4)	169 (7)
O1W—HW1B⋯N6^iv	0.82 (5)	2.07 (5)	2.859 (5)	159 (4)
Symmetry codes: (iii) x-1, y-1, z; (iv) -x, -y+2, -z+2.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022824/rz2235sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022824/rz2235Isup2.hkl

checkCIF report

Comment top

A successful strategy for preparing metal-organic supramolecular architectures is the assembly reaction between a transition d¹⁰ metal ion and two types of ligands with one acting as a bridging ligand and the other as a chelating ligand (Liu et al., 2008; Che et al., 2008). Pyrazine-2,3-dicarboxylic acid (H₂PZDC) possesses the ability to bridge and chelate metal atoms using the carboxylate oxygen atoms and nitrogen atoms (Xu et al., 2008). 1,10-Phenanthroline (phen) and its derivatives are important chelating ligands for the construction of metal-organic complexes (Che, Xu & Liu, 2006). Dipyrido[3,2-a:2',3'-c]-phenazine (DPPZ) as a phen derivative possesses potential supramolecular recognition sites for π-π aromatic stacking interactions. The present attempt at synthesizing a new zinc polymer with DPPZ and H₂PZDC gave the title complex, [Zn(DPPZ)(PZDC)(H₂O)]_n, whose structure is reported here.

The Zn atom is six-coordinated by three N atoms from one DPPZ ligand and one PZDC^2- ligand, and three O atoms from two different PZDC^2- ligands and one water molecule in a slightly distorted octahedral coordination geometry (Fig. 1). The Zn—O distances range from 2.051 (3) Å to 2.172 (3) Å and the Zn—N lengths from 2.130 (3) Å to 2.167 (3) Å (Table 1). Each PZDC^2- dianion serves as a spacer to connect adjacent metal centres into a one-dimensional chain structure parallel to the b axis. Neighbouring chains interact through π-π contacts, leading to a three-dimensional supramolecular structure (Fig. 2). There are two types of π-π interactions, occurring between adjacent DPPZ ligands (centroid-to-centroid separation = 3.732 (8) Å) and PZDC^2- anions (centroid-to-centroid separation = 3.522 (6) Å). Hydrogen bonds involving the O1W atom as donor and the N6 and O3 atoms of the PZDC^2- dianion as acceptors further stabilize the structure (Table 2).

Related literature top

For related literature, see: Che et al. (2008); Che, Li et al. (2006); Che, Xu & Liu (2006); Liu et al. (2008); Xu et al. (2008).

Experimental top

The DPPZ ligand was synthesized according to the literature method (Che, Li et al., 2006). The title compound was hydrothermally synthesized under autogenous pressure: a mixture of DPPZ, H₂PZDC, ZnNO₃ and water in a molar ratio of 1:1:1:5000 was sealed in a Teflon-lined autoclave and heated to 433 K for 3 d. Upon cooling and opening the bomb, yellow blocks of the title compound were obtained (83% yield based on Zn).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound. Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for the H atoms). [Symmetry code: (i) x, y + 1, z.]
	Fig. 2. Packing diagram of the three-dimensional supramolecular structure of the title compound formed via π-π interactions. H atoms are omitted for clarity.

catena-Poly[[aqua(dipyrido[3,2-a:2',3'-c]phenazine- κ²N⁴,N⁵)zinc(II)]-µ-pyrazine-2,3-dicarboxylato-κ³N¹,O²:O³] top

Crystal data top

[Zn(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]	Z = 2
M_r = 531.78	F(000) = 540
Triclinic, P1	D_x = 1.744 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7821 (14) Å	Cell parameters from 4412 reflections
b = 7.4349 (15) Å	θ = 3.0–27.5°
c = 20.410 (4) Å	µ = 1.27 mm⁻¹
α = 91.26 (3)°	T = 292 K
β = 95.77 (3)°	Block, yellow
γ = 98.16 (3)°	0.31 × 0.29 × 0.21 mm
V = 1012.9 (4) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4412 independent reflections
Radiation source: fine-focus sealed tube	3278 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→8
T_min = 0.681, T_max = 0.765	l = −26→26
9890 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.084P)² + 0.1727P] where P = (F_o² + 2F_c²)/3
4412 reflections	(Δ/σ)_max < 0.001
333 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Zn(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]	γ = 98.16 (3)°
M_r = 531.78	V = 1012.9 (4) Å³
Triclinic, P1	Z = 2
a = 6.7821 (14) Å	Mo Kα radiation
b = 7.4349 (15) Å	µ = 1.27 mm⁻¹
c = 20.410 (4) Å	T = 292 K
α = 91.26 (3)°	0.31 × 0.29 × 0.21 mm
β = 95.77 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4412 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3278 reflections with I > 2σ(I)
T_min = 0.681, T_max = 0.765	R_int = 0.048
9890 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.42 e Å⁻³
4412 reflections	Δρ_min = −0.58 e Å⁻³
333 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	−0.3785 (6)	0.2965 (5)	0.7826 (2)	0.0344 (9)
H1	−0.4426	0.3029	0.8206	0.041*
C2	−0.4723 (6)	0.1853 (6)	0.7307 (2)	0.0375 (10)
H2	−0.5931	0.1119	0.7349	0.045*
C3	−0.3868 (6)	0.1832 (6)	0.6728 (2)	0.0395 (10)
H3	−0.4528	0.1144	0.6364	0.047*
C4	−0.1986 (6)	0.2861 (5)	0.6690 (2)	0.0291 (8)
C5	−0.0963 (6)	0.2913 (5)	0.60945 (19)	0.0283 (8)
C6	−0.0924 (7)	0.2081 (5)	0.5015 (2)	0.0352 (9)
C7	−0.1870 (8)	0.1180 (6)	0.4421 (2)	0.0443 (11)
H7	−0.3185	0.0601	0.4400	0.053*
C8	−0.0836 (8)	0.1170 (6)	0.3880 (2)	0.0493 (12)
H8	−0.1458	0.0582	0.3491	0.059*
C9	0.1164 (9)	0.2037 (6)	0.3903 (2)	0.0514 (12)
H9	0.1845	0.2003	0.3531	0.062*
C10	0.2107 (8)	0.2921 (7)	0.4464 (2)	0.0479 (12)
H10	0.3420	0.3496	0.4471	0.058*
C11	0.1095 (7)	0.2967 (6)	0.5036 (2)	0.0379 (10)
C12	0.1042 (6)	0.3850 (5)	0.61078 (19)	0.0292 (8)
C13	0.1983 (6)	0.4856 (5)	0.67084 (19)	0.0286 (8)
C14	0.3909 (6)	0.5847 (6)	0.6747 (2)	0.0345 (9)
H14	0.4637	0.5883	0.6384	0.041*
C15	0.4710 (6)	0.6763 (6)	0.7322 (2)	0.0346 (9)
H15	0.5979	0.7444	0.7353	0.041*
C16	0.3603 (6)	0.6662 (5)	0.7859 (2)	0.0326 (9)
H16	0.4165	0.7264	0.8253	0.039*
C17	0.0958 (5)	0.4841 (5)	0.72651 (18)	0.0242 (7)
C18	−0.1092 (5)	0.3868 (5)	0.72530 (18)	0.0256 (8)
C19	0.1302 (5)	0.9551 (5)	0.89690 (18)	0.0237 (7)
C20	0.1992 (5)	1.1069 (5)	0.93824 (19)	0.0247 (8)
C21	0.2685 (6)	0.9238 (5)	1.02315 (19)	0.0288 (8)
H21	0.3121	0.9090	1.0671	0.035*
C22	0.2102 (5)	0.7712 (5)	0.98204 (19)	0.0261 (8)
H22	0.2235	0.6566	0.9978	0.031*
C23	0.0378 (6)	0.9589 (5)	0.82528 (19)	0.0271 (8)
C24	0.2040 (5)	1.3019 (5)	0.91602 (18)	0.0249 (8)
N1	−0.1984 (5)	0.3963 (4)	0.78077 (16)	0.0267 (7)
N2	0.1761 (5)	0.5730 (4)	0.78317 (15)	0.0271 (7)
N3	−0.1925 (5)	0.2047 (4)	0.55512 (17)	0.0349 (8)
N4	0.2041 (5)	0.3872 (5)	0.55828 (17)	0.0348 (8)
N5	0.1356 (4)	0.7877 (4)	0.92032 (15)	0.0234 (6)
N6	0.2640 (5)	1.0909 (4)	1.00185 (16)	0.0281 (7)
O1	−0.0880 (4)	0.8227 (4)	0.80655 (14)	0.0362 (7)
O2	0.0974 (5)	1.0921 (4)	0.79424 (15)	0.0410 (7)
O1W	−0.2753 (5)	0.5957 (5)	0.91335 (17)	0.0389 (8)
O3	0.3705 (4)	1.3872 (4)	0.91050 (17)	0.0427 (8)
O4	0.0381 (4)	1.3587 (3)	0.90882 (14)	0.0305 (6)
Zn	−0.03443 (6)	0.57612 (5)	0.85620 (2)	0.02642 (16)
HW1A	−0.368 (8)	0.552 (8)	0.909 (3)	0.054 (19)*
HW1B	−0.295 (7)	0.692 (7)	0.930 (2)	0.034 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.034 (2)	0.031 (2)	0.037 (2)	−0.0052 (17)	0.0120 (17)	−0.0021 (17)
C2	0.032 (2)	0.036 (2)	0.042 (2)	−0.0062 (18)	0.0058 (18)	−0.0039 (18)
C3	0.038 (2)	0.037 (2)	0.038 (2)	−0.0082 (19)	0.0014 (18)	−0.0108 (18)
C4	0.0326 (19)	0.0232 (18)	0.030 (2)	−0.0004 (15)	0.0040 (16)	−0.0055 (15)
C5	0.0333 (19)	0.0250 (18)	0.0254 (19)	0.0033 (16)	−0.0004 (15)	−0.0022 (15)
C6	0.047 (2)	0.032 (2)	0.027 (2)	0.0109 (19)	−0.0004 (18)	−0.0010 (16)
C7	0.058 (3)	0.040 (2)	0.032 (2)	0.008 (2)	−0.006 (2)	−0.0054 (18)
C8	0.080 (4)	0.040 (2)	0.026 (2)	0.015 (2)	−0.011 (2)	−0.0046 (18)
C9	0.082 (4)	0.043 (3)	0.032 (2)	0.011 (3)	0.019 (2)	−0.003 (2)
C10	0.065 (3)	0.048 (3)	0.033 (2)	0.011 (2)	0.013 (2)	−0.001 (2)
C11	0.050 (2)	0.034 (2)	0.030 (2)	0.007 (2)	0.0097 (19)	−0.0021 (17)
C12	0.0334 (19)	0.0291 (19)	0.025 (2)	0.0046 (16)	0.0045 (16)	−0.0019 (15)
C13	0.0273 (18)	0.0256 (19)	0.031 (2)	−0.0009 (15)	−0.0011 (15)	0.0024 (15)
C14	0.033 (2)	0.037 (2)	0.035 (2)	0.0046 (17)	0.0107 (17)	0.0014 (17)
C15	0.0257 (18)	0.039 (2)	0.037 (2)	−0.0023 (17)	0.0029 (17)	0.0059 (18)
C16	0.032 (2)	0.034 (2)	0.029 (2)	−0.0023 (17)	−0.0001 (16)	−0.0016 (16)
C17	0.0242 (17)	0.0212 (17)	0.0275 (19)	0.0049 (14)	0.0029 (14)	0.0012 (14)
C18	0.0274 (18)	0.0208 (17)	0.0273 (19)	0.0009 (14)	−0.0003 (15)	0.0009 (14)
C19	0.0223 (16)	0.0213 (17)	0.0269 (19)	−0.0007 (14)	0.0061 (14)	−0.0005 (14)
C20	0.0207 (16)	0.0185 (17)	0.034 (2)	−0.0023 (14)	0.0084 (15)	−0.0024 (15)
C21	0.0315 (18)	0.0289 (19)	0.0245 (19)	−0.0020 (16)	0.0060 (15)	−0.0003 (15)
C22	0.0281 (18)	0.0223 (17)	0.029 (2)	0.0052 (15)	0.0045 (15)	0.0031 (15)
C23	0.0302 (18)	0.0231 (18)	0.028 (2)	0.0050 (15)	0.0032 (15)	0.0015 (15)
C24	0.0307 (18)	0.0192 (16)	0.0228 (18)	−0.0046 (15)	0.0066 (15)	−0.0052 (13)
N1	0.0270 (15)	0.0228 (15)	0.0294 (17)	−0.0004 (13)	0.0050 (13)	−0.0041 (12)
N2	0.0301 (16)	0.0242 (15)	0.0240 (16)	−0.0034 (13)	−0.0008 (13)	−0.0030 (12)
N3	0.0423 (19)	0.0304 (17)	0.0305 (19)	0.0023 (15)	0.0017 (15)	−0.0043 (14)
N4	0.0417 (19)	0.0354 (18)	0.0265 (18)	0.0027 (15)	0.0038 (15)	−0.0016 (14)
N5	0.0243 (14)	0.0201 (14)	0.0260 (16)	0.0017 (12)	0.0060 (12)	0.0013 (12)
N6	0.0277 (15)	0.0260 (16)	0.0294 (17)	−0.0008 (13)	0.0049 (13)	−0.0033 (13)
O1	0.0410 (15)	0.0258 (14)	0.0365 (16)	−0.0014 (12)	−0.0119 (13)	0.0002 (12)
O2	0.0549 (19)	0.0329 (15)	0.0347 (17)	0.0005 (14)	0.0095 (14)	0.0072 (12)
O1W	0.0271 (16)	0.0357 (18)	0.052 (2)	−0.0066 (14)	0.0164 (14)	−0.0192 (15)
O3	0.0335 (15)	0.0341 (16)	0.057 (2)	−0.0112 (13)	0.0087 (14)	0.0051 (14)
O4	0.0342 (14)	0.0237 (13)	0.0367 (16)	0.0096 (11)	0.0091 (12)	0.0088 (11)
Zn	0.0313 (3)	0.0203 (2)	0.0259 (3)	−0.00162 (17)	0.00328 (17)	−0.00223 (16)

Geometric parameters (Å, º) top

C1—N1	1.341 (5)	C15—H15	0.9300
C1—C2	1.374 (6)	C16—N2	1.335 (5)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.369 (6)	C17—N2	1.345 (5)
C2—H2	0.9300	C17—C18	1.471 (5)
C3—C4	1.402 (5)	C18—N1	1.341 (5)
C3—H3	0.9300	C19—N5	1.347 (4)
C4—C18	1.393 (5)	C19—C20	1.390 (5)
C4—C5	1.457 (5)	C19—C23	1.534 (5)
C5—N3	1.332 (5)	C20—N6	1.342 (5)
C5—C12	1.435 (5)	C20—C24	1.525 (5)
C6—N3	1.344 (5)	C21—N6	1.328 (5)
C6—C7	1.420 (6)	C21—C22	1.383 (5)
C6—C11	1.429 (6)	C21—H21	0.9300
C7—C8	1.367 (7)	C22—N5	1.325 (5)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.412 (7)	C23—O2	1.229 (4)
C8—H8	0.9300	C23—O1	1.253 (5)
C9—C10	1.360 (7)	C24—O3	1.231 (4)
C9—H9	0.9300	C24—O4	1.254 (5)
C10—C11	1.414 (6)	N1—Zn	2.130 (3)
C10—H10	0.9300	N2—Zn	2.167 (3)
C11—N4	1.346 (5)	N5—Zn	2.147 (3)
C12—N4	1.324 (5)	O1—Zn	2.172 (3)
C12—C13	1.462 (5)	O1W—Zn	2.120 (3)
C13—C17	1.390 (5)	O1W—HW1A	0.66 (5)
C13—C14	1.399 (5)	O1W—HW1B	0.82 (5)
C14—C15	1.367 (6)	O4—Znⁱ	2.051 (3)
C14—H14	0.9300	Zn—O4ⁱⁱ	2.051 (3)
C15—C16	1.387 (6)

N1—C1—C2	122.7 (4)	N1—C18—C17	116.8 (3)
N1—C1—H1	118.6	C4—C18—C17	119.9 (3)
C2—C1—H1	118.6	N5—C19—C20	119.5 (3)
C3—C2—C1	119.5 (4)	N5—C19—C23	115.0 (3)
C3—C2—H2	120.2	C20—C19—C23	125.5 (3)
C1—C2—H2	120.2	N6—C20—C19	121.5 (3)
C2—C3—C4	119.2 (4)	N6—C20—C24	115.0 (3)
C2—C3—H3	120.4	C19—C20—C24	123.5 (3)
C4—C3—H3	120.4	N6—C21—C22	122.1 (4)
C18—C4—C3	117.3 (4)	N6—C21—H21	119.0
C18—C4—C5	119.9 (3)	C22—C21—H21	119.0
C3—C4—C5	122.9 (4)	N5—C22—C21	120.2 (3)
N3—C5—C12	121.8 (4)	N5—C22—H22	119.9
N3—C5—C4	118.3 (3)	C21—C22—H22	119.9
C12—C5—C4	120.0 (3)	O2—C23—O1	129.1 (4)
N3—C6—C7	119.4 (4)	O2—C23—C19	116.4 (3)
N3—C6—C11	121.2 (4)	O1—C23—C19	114.5 (3)
C7—C6—C11	119.3 (4)	O3—C24—O4	127.8 (3)
C8—C7—C6	119.6 (5)	O3—C24—C20	116.4 (3)
C8—C7—H7	120.2	O4—C24—C20	115.7 (3)
C6—C7—H7	120.2	C1—N1—C18	117.8 (3)
C7—C8—C9	121.0 (4)	C1—N1—Zn	127.4 (3)
C7—C8—H8	119.5	C18—N1—Zn	114.9 (2)
C9—C8—H8	119.5	C16—N2—C17	118.8 (3)
C10—C9—C8	120.8 (5)	C16—N2—Zn	127.2 (3)
C10—C9—H9	119.6	C17—N2—Zn	113.4 (2)
C8—C9—H9	119.6	C5—N3—C6	116.8 (4)
C9—C10—C11	120.1 (5)	C12—N4—C11	117.0 (4)
C9—C10—H10	119.9	C22—N5—C19	119.2 (3)
C11—C10—H10	119.9	C22—N5—Zn	126.6 (2)
N4—C11—C10	119.3 (4)	C19—N5—Zn	113.1 (2)
N4—C11—C6	121.5 (4)	C21—N6—C20	117.3 (3)
C10—C11—C6	119.2 (4)	C23—O1—Zn	113.8 (2)
N4—C12—C5	121.6 (4)	Zn—O1W—HW1A	129 (5)
N4—C12—C13	119.0 (3)	Zn—O1W—HW1B	123 (3)
C5—C12—C13	119.3 (3)	HW1A—O1W—HW1B	100 (6)
C17—C13—C14	118.0 (4)	C24—O4—Znⁱ	127.6 (2)
C17—C13—C12	119.8 (3)	O4ⁱⁱ—Zn—O1W	90.19 (13)
C14—C13—C12	122.2 (4)	O4ⁱⁱ—Zn—N1	90.37 (12)
C15—C14—C13	119.5 (4)	O1W—Zn—N1	96.93 (13)
C15—C14—H14	120.2	O4ⁱⁱ—Zn—N5	97.78 (12)
C13—C14—H14	120.2	O1W—Zn—N5	86.87 (13)
C14—C15—C16	119.0 (4)	N1—Zn—N5	171.02 (11)
C14—C15—H15	120.5	O4ⁱⁱ—Zn—N2	98.61 (11)
C16—C15—H15	120.5	O1W—Zn—N2	169.43 (13)
N2—C16—C15	122.4 (4)	N1—Zn—N2	77.29 (11)
N2—C16—H16	118.8	N5—Zn—N2	97.65 (12)
C15—C16—H16	118.8	O4ⁱⁱ—Zn—O1	174.40 (11)
N2—C17—C13	122.3 (3)	O1W—Zn—O1	90.70 (13)
N2—C17—C18	116.9 (3)	N1—Zn—O1	95.01 (11)
C13—C17—C18	120.8 (3)	N5—Zn—O1	76.76 (11)
N1—C18—C4	123.3 (3)	N2—Zn—O1	81.10 (12)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW1A···O3ⁱⁱⁱ	0.66 (5)	2.01 (5)	2.662 (4)	169 (7)
O1W—HW1B···N6^iv	0.82 (5)	2.07 (5)	2.859 (5)	159 (4)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]
M_r	531.78
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	6.7821 (14), 7.4349 (15), 20.410 (4)
α, β, γ (°)	91.26 (3), 95.77 (3), 98.16 (3)
V (Å³)	1012.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.31 × 0.29 × 0.21

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.681, 0.765
No. of measured, independent and observed [I > 2σ(I)] reflections	9890, 4412, 3278
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.148, 1.07
No. of reflections	4412
No. of parameters	333
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.58

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

N1—Zn	2.130 (3)	O1—Zn	2.172 (3)
N2—Zn	2.167 (3)	O1W—Zn	2.120 (3)
N5—Zn	2.147 (3)	O4—Znⁱ	2.051 (3)

O4ⁱⁱ—Zn—O1W	90.19 (13)	O1W—Zn—N5	86.87 (13)
O4ⁱⁱ—Zn—N1	90.37 (12)	N1—Zn—N5	171.02 (11)
O1W—Zn—N1	96.93 (13)	O4ⁱⁱ—Zn—N2	98.61 (11)
O4ⁱⁱ—Zn—N5	97.78 (12)	O1W—Zn—N2	169.43 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW1A···O3ⁱⁱⁱ	0.66 (5)	2.01 (5)	2.662 (4)	169 (7)
O1W—HW1B···N6^iv	0.82 (5)	2.07 (5)	2.859 (5)	159 (4)

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

Acknowledgements

The authors thank the Doctoral Foundation of Jilin Normal University (grant Nos. 2006006 and 2007009) and the Subject and Base Construction Foundation of Jilin Normal University (grant No. 2006041).

References

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