catena-Poly[[(1,10-phenanthroline-κ2N,N′)zinc]-μ-furan-2,5-dicarboxyl­ato-κ4O2,O2′:O5,O5′]

Li, Y.-F.; Xu, Y.; Qin, X.-L.; Gao, W.-Y.; Gao, Y.

doi:10.1107/S1600536812019836

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m750

doi:10.1107/S1600536812019836

Open

access

catena-Poly[[(1,10-phenanthroline-κ²N,N′)zinc]-μ-furan-2,5-dicarboxylato-κ⁴O²,O^2′:O⁵,O^5′]

Ya-Feng Li,^a ^* Yue Xu,^a Xiao-Lin Qin,^a Wen-Yuan Gao ^a and Yue Gao ^a

^aSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: fly012345@sohu.com

(Received 30 April 2012; accepted 3 May 2012; online 12 May 2012)

In the title coordination polymer, [Zn(C₆H₂O₅)(C₁₂H₈N₂)]_n, an infinite chain is formed along [010] by linking the chelated {Zn(phen)} entities (phen is 1,10-phenanthroline) with two carboxylate groups of the furan-2,5-dicarboxylate ligand. The Zn^II atom shows trigonal–prismatic coordination.

Related literature

For related structures, see: Li, Gao et al. (2012 ); Li, Xu et al. (2012 ).

Experimental

Crystal data

[Zn(C₆H₂O₅)(C₁₂H₈N₂)]
M_r = 399.67
Monoclinic, P 2₁ /c
a = 5.8725 (10) Å
b = 15.013 (3) Å
c = 19.241 (8) Å
β = 104.42 (3)°
V = 1642.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.53 mm⁻¹
T = 293 K
0.16 × 0.13 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.792, T_max = 0.838
14467 measured reflections
3688 independent reflections
2166 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.121
S = 1.04
3688 reflections
235 parameters
156 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812019836/ng5269sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019836/ng5269Isup2.hkl

checkCIF report

Comment top

Recently, we utilized furan-2,5-dicarboxyl icacid as the ligand to constructed the MOFs (Li, Gao et al. 2012; Li, Xu et al., 2012). In this work, a chainlike compound, [Zn(C₁₂H₈N₂)(C₆H₂O₅)]_n (I), is reported.

The asymmetric unit consists of one Zn cation, one furan-2,5-dicarboxylate anion and one C₁₂H₈N₂ (Fig.1). The Zn cation is coordinated by four carboxylate O atoms, two nitrogen of one C₁₂H₈N₂, exhibiting triganol prismatic coordination. The furan-2,5-dicarboxylate shows a µ₂:η¹,η¹;η¹,η¹ coordinating mode. The dihedral angles of two furan rings versus. C₆H₂O₅ ring and two furan rings, which are coordinated to the same Zn cation, are 52.06 (12)°, 62.18 (11)° and 88.27 (12)°, respectively.

TheZn cations are linked by two carboxylate of furan-2,5-dicarboxylate to give rise to an infinite chain (Fig. 2). The adjacent chains are piled up along [100] through π-π interactions between C₁₂H₈N₂ molecules of different chains. vVan der Waals forces exist between the layers (Fig. 3).

Related literature top

For related structures, see: Li, Gao et al. (2012); Li, Xu et al. (2012).

Experimental top

Furan-2,5-dicarboxylic acid (0.0156 g, 0.10 mmol), Zn(NO₃)₂^.6H₂O (0.0298 g, 0.10 mmol), and C₁₂H₈N₂ (0.0198, 0.11 mmol) were dissolved in DMF (5 ml, 48 mmol) under stirring. The mixture with molar ratio of 1 (furan-2,5-dicarboxyl acid): 1 (Zn(NO₃)₂^.6H₂O): 1.1 (C₁₂H₈N₂): 480 DMI was heated under 120°C for 2 days. Colorless blocks were collected as a single phase.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The unit cell of (I), showing the atomic labelling scheme and displacement ellipsoids at the 50% probability level. [Symmetry codes: (i) 1 - x, -0.5 + y, 0.5 - z.]
	Fig. 2. The stick plot of (I), displaying the infinite chain along [010] direction formed by linking the Zn with two carboxyls of furan-2,5-dicarboxylate.
	Fig. 3. The ball-stick packing diagram of (I). The adjacent chains are piled up along [100] through π-π interactions between C₁₂H₈N₂ molecules of different chains.

catena-Poly[[(1,10-phenanthroline-κ²N,N')zinc]- µ-furan-2,5-dicarboxylato- κ⁴O²,O^2':O⁵,O^5'] top

Crystal data top

[Zn(C₆H₂O₅)(C₁₂H₈N₂)]	F(000) = 808
M_r = 399.67	D_x = 1.616 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 5.8725 (10) Å	θ = 3.5–27.5°
b = 15.013 (3) Å	µ = 1.53 mm⁻¹
c = 19.241 (8) Å	T = 293 K
β = 104.42 (3)°	Block, colorless
V = 1642.9 (8) Å³	0.16 × 0.13 × 0.12 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3688 independent reflections
Radiation source: fine-focus sealed tube	2166 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 3.5°
ω scans	h = −7→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
T_min = 0.792, T_max = 0.838	l = −24→24
14467 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0305P)² + 1.7497P] where P = (F_o² + 2F_c²)/3
3688 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.37 e Å⁻³
156 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Zn(C₆H₂O₅)(C₁₂H₈N₂)]	V = 1642.9 (8) Å³
M_r = 399.67	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.8725 (10) Å	µ = 1.53 mm⁻¹
b = 15.013 (3) Å	T = 293 K
c = 19.241 (8) Å	0.16 × 0.13 × 0.12 mm
β = 104.42 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3688 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2166 reflections with I > 2σ(I)
T_min = 0.792, T_max = 0.838	R_int = 0.066
14467 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	156 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	Δρ_max = 0.37 e Å⁻³
3688 reflections	Δρ_min = −0.37 e Å⁻³
235 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
Zn1	0.35240 (10)	0.25875 (4)	0.08732 (3)	0.0611 (2)
O1	0.6391 (5)	0.3452 (2)	0.11677 (17)	0.0704 (9)
O2	0.3330 (5)	0.3794 (2)	0.15596 (16)	0.0662 (9)
O3	0.5760 (4)	0.51458 (17)	0.23919 (13)	0.0448 (6)
O4	0.8463 (5)	0.6748 (2)	0.36985 (15)	0.0636 (8)
O5	0.4722 (5)	0.6501 (2)	0.32328 (16)	0.0686 (9)
N1	0.1045 (7)	0.3030 (3)	−0.00407 (19)	0.0614 (9)
N2	0.4670 (6)	0.1904 (3)	0.00778 (18)	0.0606 (10)
C1	0.5395 (7)	0.3928 (3)	0.1538 (2)	0.0503 (10)
C2	0.6835 (6)	0.4618 (3)	0.1988 (2)	0.0437 (9)
C3	0.9155 (7)	0.4798 (3)	0.2139 (2)	0.0565 (11)
H3	1.0259	0.4532	0.1933	0.068*
C4	0.9582 (7)	0.5469 (3)	0.2670 (2)	0.0544 (11)
H4	1.1028	0.5724	0.2886	0.065*
C5	0.7492 (6)	0.5669 (3)	0.28057 (19)	0.0444 (9)
C6	0.6828 (7)	0.6332 (3)	0.3271 (2)	0.0484 (10)
C7	−0.0749 (10)	0.3570 (4)	−0.0079 (3)	0.0833 (16)
H7	−0.0992	0.3816	0.0340	0.100*
C8	−0.2319 (10)	0.3783 (4)	−0.0746 (4)	0.0997 (19)
H8	−0.3571	0.4170	−0.0767	0.120*
C9	−0.1958 (10)	0.3409 (4)	−0.1357 (3)	0.0943 (19)
H9	−0.2991	0.3539	−0.1797	0.113*
C10	−0.0086 (9)	0.2843 (4)	−0.1334 (3)	0.0711 (14)
C11	0.0446 (11)	0.2424 (4)	−0.1952 (2)	0.0849 (17)
H11	−0.0532	0.2524	−0.2405	0.102*
C12	0.2292 (12)	0.1902 (4)	−0.1882 (3)	0.0942 (18)
H12	0.2631	0.1667	−0.2293	0.113*
C13	0.3771 (10)	0.1689 (4)	−0.1206 (3)	0.0757 (14)
C14	0.5738 (13)	0.1132 (5)	−0.1103 (4)	0.107 (2)
H14	0.6125	0.0874	−0.1497	0.129*
C15	0.7072 (12)	0.0968 (5)	−0.0442 (4)	0.112 (2)
H15	0.8534	0.0666	−0.0303	0.135*
C16	0.6508 (9)	0.1371 (4)	0.0144 (3)	0.0880 (17)
H16	0.7459	0.1262	0.0601	0.106*
C17	0.1378 (7)	0.2662 (3)	−0.0654 (2)	0.0542 (11)
C18	0.3306 (8)	0.2074 (3)	−0.0590 (2)	0.0574 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0831 (4)	0.0578 (3)	0.0401 (3)	−0.0158 (3)	0.0106 (2)	−0.0017 (2)
O1	0.0689 (19)	0.066 (2)	0.082 (2)	−0.0051 (16)	0.0292 (17)	−0.0279 (17)
O2	0.0538 (18)	0.079 (2)	0.068 (2)	−0.0167 (15)	0.0205 (15)	−0.0220 (16)
O3	0.0420 (14)	0.0468 (16)	0.0452 (14)	−0.0007 (11)	0.0099 (11)	−0.0086 (12)
O4	0.0610 (18)	0.064 (2)	0.0605 (18)	−0.0104 (15)	0.0055 (14)	−0.0212 (15)
O5	0.0543 (18)	0.082 (2)	0.0668 (19)	0.0076 (16)	0.0109 (15)	−0.0272 (17)
N1	0.071 (2)	0.061 (2)	0.054 (2)	0.0000 (19)	0.0195 (18)	0.0055 (18)
N2	0.062 (2)	0.063 (2)	0.053 (2)	−0.0052 (19)	0.0054 (18)	−0.0020 (18)
C1	0.056 (2)	0.048 (2)	0.045 (2)	0.0009 (19)	0.0110 (19)	−0.0012 (18)
C2	0.046 (2)	0.043 (2)	0.044 (2)	0.0021 (16)	0.0130 (17)	−0.0064 (17)
C3	0.045 (2)	0.058 (3)	0.068 (3)	0.0036 (19)	0.018 (2)	−0.004 (2)
C4	0.042 (2)	0.055 (3)	0.063 (3)	−0.0041 (18)	0.008 (2)	−0.007 (2)
C5	0.045 (2)	0.042 (2)	0.043 (2)	−0.0048 (17)	0.0061 (17)	−0.0030 (16)
C6	0.052 (2)	0.047 (2)	0.045 (2)	0.0031 (18)	0.0118 (19)	−0.0031 (17)
C7	0.092 (4)	0.085 (4)	0.083 (4)	0.008 (3)	0.040 (3)	0.012 (3)
C8	0.083 (4)	0.101 (5)	0.117 (5)	0.020 (3)	0.028 (4)	0.033 (4)
C9	0.082 (4)	0.109 (5)	0.080 (4)	−0.005 (3)	−0.002 (3)	0.031 (3)
C10	0.075 (3)	0.073 (3)	0.057 (3)	−0.015 (3)	0.002 (2)	0.016 (2)
C11	0.113 (4)	0.096 (4)	0.037 (2)	−0.030 (3)	0.002 (3)	0.001 (3)
C12	0.141 (5)	0.094 (4)	0.051 (3)	−0.019 (4)	0.030 (3)	−0.010 (3)
C13	0.101 (4)	0.064 (3)	0.065 (3)	−0.014 (3)	0.027 (3)	−0.012 (2)
C14	0.137 (5)	0.091 (4)	0.108 (5)	0.007 (4)	0.056 (4)	−0.022 (4)
C15	0.110 (5)	0.107 (5)	0.129 (5)	0.028 (4)	0.046 (4)	−0.001 (4)
C16	0.076 (3)	0.086 (4)	0.096 (4)	0.009 (3)	0.009 (3)	0.003 (3)
C17	0.065 (3)	0.057 (3)	0.039 (2)	−0.014 (2)	0.0092 (19)	0.0027 (18)
C18	0.072 (3)	0.056 (3)	0.045 (2)	−0.016 (2)	0.015 (2)	−0.0059 (19)

Geometric parameters (Å, º) top

Zn1—O4ⁱ	2.027 (3)	C5—C6	1.455 (5)
Zn1—N2	2.089 (4)	C7—C8	1.418 (7)
Zn1—O1	2.090 (3)	C7—H7	0.9300
Zn1—N1	2.092 (4)	C8—C9	1.367 (8)
Zn1—O2	2.261 (3)	C8—H8	0.9300
Zn1—O5ⁱ	2.408 (3)	C9—C10	1.381 (8)
O1—C1	1.252 (5)	C9—H9	0.9300
O2—C1	1.240 (5)	C10—C17	1.401 (6)
O3—C2	1.369 (4)	C10—C11	1.447 (7)
O3—C5	1.372 (4)	C11—C12	1.317 (8)
O4—C6	1.263 (4)	C11—H11	0.9300
O5—C6	1.246 (4)	C12—C13	1.410 (7)
N1—C7	1.316 (6)	C12—H12	0.9300
N1—C17	1.361 (5)	C13—C14	1.399 (8)
N2—C16	1.324 (6)	C13—C18	1.405 (6)
N2—C18	1.358 (5)	C14—C15	1.341 (9)
C1—C2	1.475 (5)	C14—H14	0.9300
C2—C3	1.347 (5)	C15—C16	1.390 (8)
C3—C4	1.413 (6)	C15—H15	0.9487
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.351 (5)	C17—C18	1.416 (6)
C4—H4	0.9300

O4ⁱ—Zn1—N2	108.37 (14)	C4—C3—H3	126.7
O4ⁱ—Zn1—O1	141.51 (13)	C5—C4—C3	107.0 (4)
N2—Zn1—O1	96.85 (13)	C5—C4—H4	126.5
O4ⁱ—Zn1—N1	100.88 (13)	C3—C4—H4	126.5
N2—Zn1—N1	79.86 (15)	C4—C5—O3	109.8 (3)
O1—Zn1—N1	112.06 (14)	C4—C5—C6	131.8 (4)
O4ⁱ—Zn1—O2	98.21 (12)	O3—C5—C6	118.4 (3)
N2—Zn1—O2	153.40 (13)	O5—C6—O4	121.3 (4)
O1—Zn1—O2	59.89 (11)	O5—C6—C5	121.1 (4)
N1—Zn1—O2	96.36 (14)	O4—C6—C5	117.5 (3)
O4ⁱ—Zn1—O5ⁱ	58.36 (10)	O5—C6—Zn1ⁱⁱ	69.4 (2)
N2—Zn1—O5ⁱ	91.83 (13)	O4—C6—Zn1ⁱⁱ	51.9 (2)
O1—Zn1—O5ⁱ	93.13 (12)	C5—C6—Zn1ⁱⁱ	169.1 (3)
N1—Zn1—O5ⁱ	154.14 (13)	N1—C7—C8	121.4 (5)
O2—Zn1—O5ⁱ	101.54 (12)	N1—C7—H7	119.3
O4ⁱ—Zn1—C1	121.27 (13)	C8—C7—H7	119.3
N2—Zn1—C1	126.34 (14)	C9—C8—C7	118.8 (6)
O1—Zn1—C1	30.16 (12)	C9—C8—H8	120.6
N1—Zn1—C1	107.51 (14)	C7—C8—H8	120.6
O2—Zn1—C1	29.78 (11)	C8—C9—C10	121.1 (5)
O5ⁱ—Zn1—C1	97.18 (12)	C8—C9—H9	119.4
O4ⁱ—Zn1—C6ⁱ	29.39 (11)	C10—C9—H9	119.4
N2—Zn1—C6ⁱ	101.69 (14)	C9—C10—C17	116.6 (5)
O1—Zn1—C6ⁱ	118.33 (13)	C9—C10—C11	125.1 (5)
N1—Zn1—C6ⁱ	128.86 (14)	C17—C10—C11	118.3 (5)
O2—Zn1—C6ⁱ	101.04 (13)	C12—C11—C10	121.1 (5)
O5ⁱ—Zn1—C6ⁱ	28.98 (10)	C12—C11—H11	119.4
C1—Zn1—C6ⁱ	111.29 (13)	C10—C11—H11	119.4
C1—O1—Zn1	92.8 (2)	C11—C12—C13	122.1 (6)
C1—O2—Zn1	85.3 (2)	C11—C12—H12	119.0
C2—O3—C5	106.3 (3)	C13—C12—H12	119.0
C6—O4—Zn1ⁱⁱ	98.7 (2)	C14—C13—C18	116.9 (5)
C6—O5—Zn1ⁱⁱ	81.6 (2)	C14—C13—C12	124.3 (6)
C7—N1—C17	119.2 (4)	C18—C13—C12	118.7 (5)
C7—N1—Zn1	128.5 (4)	C15—C14—C13	120.8 (6)
C17—N1—Zn1	112.3 (3)	C15—C14—H14	119.6
C16—N2—C18	118.7 (4)	C13—C14—H14	119.6
C16—N2—Zn1	129.0 (4)	C14—C15—C16	119.2 (6)
C18—N2—Zn1	112.3 (3)	C14—C15—H15	129.0
O2—C1—O1	121.8 (4)	C16—C15—H15	111.2
O2—C1—C2	121.1 (4)	N2—C16—C15	122.5 (6)
O1—C1—C2	117.0 (4)	N2—C16—H16	118.7
O2—C1—Zn1	64.9 (2)	C15—C16—H16	118.7
O1—C1—Zn1	57.0 (2)	N1—C17—C10	122.9 (4)
C2—C1—Zn1	170.2 (3)	N1—C17—C18	117.5 (4)
C3—C2—O3	110.2 (3)	C10—C17—C18	119.6 (4)
C3—C2—C1	132.0 (4)	N2—C18—C13	121.8 (5)
O3—C2—C1	117.5 (3)	N2—C18—C17	118.0 (4)
C2—C3—C4	106.7 (4)	C13—C18—C17	120.1 (4)
C2—C3—H3	126.7

O4ⁱ—Zn1—O1—C1	−59.7 (3)	O2—C1—C2—C3	168.7 (4)
N2—Zn1—O1—C1	168.9 (3)	O1—C1—C2—C3	−7.3 (7)
N1—Zn1—O1—C1	87.1 (3)	O2—C1—C2—O3	−4.5 (6)
O2—Zn1—O1—C1	2.6 (2)	O1—C1—C2—O3	179.6 (4)
O5ⁱ—Zn1—O1—C1	−98.9 (3)	O3—C2—C3—C4	0.5 (5)
C6ⁱ—Zn1—O1—C1	−83.9 (3)	C1—C2—C3—C4	−173.0 (4)
O4ⁱ—Zn1—O2—C1	143.5 (2)	C2—C3—C4—C5	−0.9 (5)
N2—Zn1—O2—C1	−34.5 (4)	C3—C4—C5—O3	0.9 (5)
O1—Zn1—O2—C1	−2.6 (2)	C3—C4—C5—C6	−176.6 (4)
N1—Zn1—O2—C1	−114.5 (3)	C2—O3—C5—C4	−0.6 (4)
O5ⁱ—Zn1—O2—C1	84.3 (3)	C2—O3—C5—C6	177.3 (3)
C6ⁱ—Zn1—O2—C1	113.8 (3)	Zn1ⁱⁱ—O5—C6—O4	1.0 (4)
O4ⁱ—Zn1—N1—C7	71.3 (4)	Zn1ⁱⁱ—O5—C6—C5	−176.7 (4)
N2—Zn1—N1—C7	178.3 (4)	Zn1ⁱⁱ—O4—C6—O5	−1.2 (5)
O1—Zn1—N1—C7	−88.4 (4)	Zn1ⁱⁱ—O4—C6—C5	176.6 (3)
O2—Zn1—N1—C7	−28.3 (4)	C4—C5—C6—O5	168.5 (4)
O5ⁱ—Zn1—N1—C7	105.4 (5)	O3—C5—C6—O5	−8.9 (6)
C1—Zn1—N1—C7	−56.6 (4)	C4—C5—C6—O4	−9.3 (7)
C6ⁱ—Zn1—N1—C7	81.4 (5)	O3—C5—C6—O4	173.3 (3)
O4ⁱ—Zn1—N1—C17	−106.0 (3)	C4—C5—C6—Zn1ⁱⁱ	4.8 (19)
N2—Zn1—N1—C17	1.0 (3)	O3—C5—C6—Zn1ⁱⁱ	−172.5 (13)
O1—Zn1—N1—C17	94.3 (3)	C17—N1—C7—C8	−0.8 (7)
O2—Zn1—N1—C17	154.4 (3)	Zn1—N1—C7—C8	−178.0 (4)
O5ⁱ—Zn1—N1—C17	−71.9 (4)	N1—C7—C8—C9	0.7 (9)
C1—Zn1—N1—C17	126.1 (3)	C7—C8—C9—C10	−0.9 (9)
C6ⁱ—Zn1—N1—C17	−95.9 (3)	C8—C9—C10—C17	1.2 (8)
O4ⁱ—Zn1—N2—C16	−84.1 (4)	C8—C9—C10—C11	−179.5 (5)
O1—Zn1—N2—C16	66.4 (4)	C9—C10—C11—C12	179.0 (6)
N1—Zn1—N2—C16	177.7 (4)	C17—C10—C11—C12	−1.7 (8)
O2—Zn1—N2—C16	93.7 (5)	C10—C11—C12—C13	3.3 (9)
O5ⁱ—Zn1—N2—C16	−27.0 (4)	C11—C12—C13—C14	179.4 (6)
C1—Zn1—N2—C16	73.3 (5)	C11—C12—C13—C18	−2.5 (9)
C6ⁱ—Zn1—N2—C16	−54.5 (4)	C18—C13—C14—C15	1.2 (9)
O4ⁱ—Zn1—N2—C18	97.8 (3)	C12—C13—C14—C15	179.4 (6)
O1—Zn1—N2—C18	−111.7 (3)	C13—C14—C15—C16	−1.2 (11)
N1—Zn1—N2—C18	−0.4 (3)	C18—N2—C16—C15	−1.1 (8)
O2—Zn1—N2—C18	−84.3 (4)	Zn1—N2—C16—C15	−179.1 (5)
O5ⁱ—Zn1—N2—C18	154.9 (3)	C14—C15—C16—N2	1.2 (10)
C1—Zn1—N2—C18	−104.8 (3)	C7—N1—C17—C10	1.2 (7)
C6ⁱ—Zn1—N2—C18	127.5 (3)	Zn1—N1—C17—C10	178.8 (3)
Zn1—O2—C1—O1	4.5 (4)	C7—N1—C17—C18	−179.0 (4)
Zn1—O2—C1—C2	−171.2 (4)	Zn1—N1—C17—C18	−1.4 (5)
Zn1—O1—C1—O2	−4.9 (4)	C9—C10—C17—N1	−1.4 (7)
Zn1—O1—C1—C2	171.0 (3)	C11—C10—C17—N1	179.2 (4)
O4ⁱ—Zn1—C1—O2	−43.5 (3)	C9—C10—C17—C18	178.9 (4)
N2—Zn1—C1—O2	161.7 (2)	C11—C10—C17—C18	−0.5 (6)
O1—Zn1—C1—O2	175.4 (4)	C16—N2—C18—C13	1.2 (7)
N1—Zn1—C1—O2	71.5 (3)	Zn1—N2—C18—C13	179.5 (3)
O5ⁱ—Zn1—C1—O2	−100.7 (2)	C16—N2—C18—C17	−178.5 (4)
C6ⁱ—Zn1—C1—O2	−74.5 (3)	Zn1—N2—C18—C17	−0.2 (5)
O4ⁱ—Zn1—C1—O1	141.0 (2)	C14—C13—C18—N2	−1.2 (7)
N2—Zn1—C1—O1	−13.8 (3)	C12—C13—C18—N2	−179.5 (5)
N1—Zn1—C1—O1	−103.9 (3)	C14—C13—C18—C17	178.5 (5)
O2—Zn1—C1—O1	−175.4 (4)	C12—C13—C18—C17	0.2 (7)
O5ⁱ—Zn1—C1—O1	83.8 (3)	N1—C17—C18—N2	1.1 (6)
C6ⁱ—Zn1—C1—O1	110.1 (3)	C10—C17—C18—N2	−179.1 (4)
C5—O3—C2—C3	0.0 (4)	N1—C17—C18—C13	−178.6 (4)
C5—O3—C2—C1	174.6 (3)	C10—C17—C18—C13	1.2 (6)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₆H₂O₅)(C₁₂H₈N₂)]
M_r	399.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.8725 (10), 15.013 (3), 19.241 (8)
β (°)	104.42 (3)
V (Å³)	1642.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.53
Crystal size (mm)	0.16 × 0.13 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.792, 0.838
No. of measured, independent and observed [I > 2σ(I)] reflections	14467, 3688, 2166
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.121, 1.04
No. of reflections	3688
No. of parameters	235
No. of restraints	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.37

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000).

Acknowledgements

This project was sponsored by the Scientific Research Foundation for the Returned Overseas Team, Chinese Education Ministry.

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Li, Y.-F., Gao, Y., Xu, Y., Qin, X. & Gao, W.-Y. (2012). Acta Cryst. E68, m445. CSD CrossRef IUCr Journals Google Scholar
Li, Y.-F., Xu, Y., Qin, X.-L., Gao, W.-Y. & Gao, Y. (2012). Acta Cryst. E68, m659. CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.