catena-Poly[[(nitrato-κ2O,O′)silver(I)]-μ-N,N′-bis­(3-pyridyl­methyl­idene)benzene-1,4-diamine]

Liu, Y.-H.; Xu, Q.; Han, Z.-Y.

doi:10.1107/S1600536810025997

metal-organic compounds

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Volume 66| Part 8| August 2010| Page m903

https://doi.org/10.1107/S1600536810025997

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catena-Poly[[(nitrato-κ²O,O′)silver(I)]-μ-N,N′-bis(3-pyridylmethylidene)benzene-1,4-diamine]

Yong-Hao Liu,^a ^* Quan Xu ^a and Zhi-You Han ^a

^aDepartment of Physics, Daqing Normal University, Daqing, 163712, People's Republic of China
^*Correspondence e-mail: yonghaoliu1980@163.com

(Received 13 June 2010; accepted 1 July 2010; online 7 July 2010)

In the title compound, [Ag(NO₃)(C₁₈H₁₄N₄)]_n, the Ag^I atom is coordinated by two N atoms from two N,N′-bis(3-pyridylmethylidene)benzene-1,4-diamine (bpbd) molecules and two O atoms from a bidentate nitrate anion. The bpbd molecules bridge the Ag atoms into a chain. Two adjacent chains are further connected by Ag⋯Ag interactions [3.1631 (8) Å], forming a double-chain structure. A π–π interaction [centroid–centroid distance = 3.758 (3) Å] occurs between the double chains. Interchain C—H⋯O hydrogen bonds are observed.

Related literature

For general background to metal–organic frameworks with bipyridine-type ligands, see: Biradha et al. (2006 ); Cunha-Silva et al. (2006 ); Lu et al. (2002 ); Ye et al. (2004 ).

Experimental

Crystal data

[Ag(NO₃)(C₁₈H₁₄N₄)]
M_r = 456.21
Triclinic, $[P \overline 1]$
a = 9.2148 (18) Å
b = 9.771 (2) Å
c = 10.800 (2) Å
α = 81.51 (3)°
β = 74.27 (3)°
γ = 66.52 (3)°
V = 857.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 293 K
0.31 × 0.30 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.705, T_max = 0.908
8493 measured reflections
3891 independent reflections
3163 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.094
S = 1.10
3891 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N1	2.162 (2)
Ag1—N4ⁱ	2.163 (2)
Ag1—O2	2.731 (3)
Ag1—O3	2.704 (3)
Symmetry code: (i) x+2, y-1, z-1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3ⁱⁱ	0.93	2.50	3.276 (4)	141
C16—H16A⋯O2ⁱⁱⁱ	0.93	2.44	3.280 (4)	151
Symmetry codes: (ii) -x+3, -y, -z+1; (iii) -x+1, -y+2, -z+2.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810025997/hy2324sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025997/hy2324Isup2.hkl

checkCIF report

Comment top

Bipyridine-type ligands have been extensively investigated in recent years, owing to their simple structures, readily availabilities and more predictable formation of network structures (Biradha et al., 2006; Cunha-Silva et al., 2006; Lu et al., 2002). Moreover, when introducing double Schiff-base, a great deal of metal–organic frameworks with unusual network patterns and novel properties can be achieved due to the specific geometry including the different relative orientation of N-donors and the zigzag conformation of the space moiety between the two terminal coordination groups (Ye et al., 2004).

Herein, we choose 3,3'-bipyridine-type Schiff-base as an organic linking ligand. In this simple compound, N═C—H group can act as a hydrogen bonding donor and the pyridyl N atom as an acceptor. In the title complex, the ligand takes a bidentate bridging coordination fashion and links two Ag^I centers with two pyridyl N atoms (Fig. 1), forming a zigzag chain, with Ag—N distances being 2.162 (2) and 2.163 (2) Å (Table 1). The two neighboring Ag atoms exhibit an Ag···Ag interaction, with a distance of 3.1631 (8) Å. The Ag atoms are also coordinated by distant nitrate O atoms [Ag—O = 2.731 (3) and 2.704 (3) Å], leading to a deviation from linearity [N—Ag—N = 159.44 (9)°]. Two adjacent chains are connected by the Ag···Ag interactions into a double-chain structure (Fig. 2). A π–π interaction [centroid–centroid distance = 3.758 (3) Å] occurs between the double-chains. Interchain C—H···O hydrogen bonds are observed (Table 2).

Related literature top

For general background to metal–organic frameworks with bipyridine-type ligands, see: Biradha et al. (2006); Cunha-Silva et al. (2006); Lu et al. (2002); Ye et al. (2004).

Experimental top

The ligand L was prepared according to the previous method (Ye et al., 2004). 1,4-Diaminobenzene (2.14 mg, 10 mmol) was dissolved in methanol (20 ml), followed by addition of 3-pyridinecarboxaldehyde (4.24 mg, 40 mmol). The mixture was stirred at room temperature for 2 h and filtered. The resulting yellow crystalline solid was washed with methanol several times and dried in air. A solution of AgNO₃ (33.9 mg, 0.2 mmol) in acetonitrile (10 ml) was slowly layered onto a solution of L (117 mg, 0.625 mmol) in methylene chloride (10 ml). Diffusion between the two phases over a week produced colorless crystals.

Structure description top

For general background to metal–organic frameworks with bipyridine-type ligands, see: Biradha et al. (2006); Cunha-Silva et al. (2006); Lu et al. (2002); Ye et al. (2004).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids shown at the 50% probability level. [Symmetry codes: (i) 2+x, -1+y, -1+z; (ii) -2+x, 1+y, 1+z.]
	Fig. 2. A view of the double-chain structure in the title compound.

catena-Poly[[(nitrato-κ²O,O')silver(I)]-µ- N,N'-bis(3-pyridylmethylidene)benzene-1,4-diamine] top

Crystal data top

[Ag(NO₃)(C₁₈H₁₄N₄)]	Z = 2
M_r = 456.21	F(000) = 456
Triclinic, P1	D_x = 1.767 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2148 (18) Å	Cell parameters from 3891 reflections
b = 9.771 (2) Å	θ = 3.1–27.5°
c = 10.800 (2) Å	µ = 1.21 mm⁻¹
α = 81.51 (3)°	T = 293 K
β = 74.27 (3)°	Block, colorless
γ = 66.52 (3)°	0.31 × 0.30 × 0.08 mm
V = 857.6 (4) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3891 independent reflections
Radiation source: fine-focus sealed tube	3163 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
T_min = 0.705, T_max = 0.908	l = −13→14
8493 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.059P)²] where P = (F_o² + 2F_c²)/3
3891 reflections	(Δ/σ)_max = 0.002
244 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Ag(NO₃)(C₁₈H₁₄N₄)]	γ = 66.52 (3)°
M_r = 456.21	V = 857.6 (4) Å³
Triclinic, P1	Z = 2
a = 9.2148 (18) Å	Mo Kα radiation
b = 9.771 (2) Å	µ = 1.21 mm⁻¹
c = 10.800 (2) Å	T = 293 K
α = 81.51 (3)°	0.31 × 0.30 × 0.08 mm
β = 74.27 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3891 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3163 reflections with I > 2σ(I)
T_min = 0.705, T_max = 0.908	R_int = 0.019
8493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.10	Δρ_max = 0.72 e Å⁻³
3891 reflections	Δρ_min = −0.29 e Å⁻³
244 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	1.45799 (2)	0.37548 (2)	0.45603 (2)	0.05309 (11)
N1	1.2254 (3)	0.3738 (2)	0.5682 (2)	0.0379 (5)
N2	0.6797 (3)	0.6198 (2)	0.8049 (2)	0.0394 (5)
N3	0.1476 (3)	1.1322 (2)	1.0027 (2)	0.0451 (5)
N4	−0.3549 (3)	1.3921 (2)	1.2898 (2)	0.0409 (5)
N5	1.7214 (3)	0.1260 (3)	0.5841 (3)	0.0519 (6)
O1	1.8206 (4)	0.0262 (4)	0.6349 (3)	0.0910 (9)
O2	1.6959 (3)	0.2598 (3)	0.5904 (3)	0.0794 (8)
O3	1.6440 (4)	0.0949 (3)	0.5224 (3)	0.0686 (7)
C1	1.2039 (3)	0.2446 (3)	0.5801 (3)	0.0447 (6)
H1A	1.2915	0.1601	0.5462	0.054*
C2	1.0576 (4)	0.2313 (3)	0.6405 (3)	0.0530 (7)
H2A	1.0457	0.1405	0.6437	0.064*
C3	0.9290 (3)	0.3543 (3)	0.6960 (3)	0.0468 (6)
H3A	0.8302	0.3470	0.7394	0.056*
C4	0.9491 (3)	0.4889 (3)	0.6862 (2)	0.0338 (5)
C5	1.0982 (3)	0.4942 (3)	0.6205 (2)	0.0358 (5)
H5A	1.1113	0.5850	0.6119	0.043*
C6	0.8148 (3)	0.6244 (3)	0.7420 (2)	0.0373 (5)
H6A	0.8299	0.7145	0.7306	0.045*
C7	0.5498 (3)	0.7521 (3)	0.8539 (2)	0.0356 (5)
C8	0.4388 (3)	0.7368 (3)	0.9655 (3)	0.0426 (6)
H8A	0.4528	0.6424	1.0046	0.051*
C9	0.3077 (3)	0.8597 (3)	1.0195 (3)	0.0464 (7)
H9A	0.2364	0.8481	1.0960	0.056*
C10	0.2824 (3)	1.0000 (3)	0.9596 (2)	0.0379 (5)
C11	0.3917 (4)	1.0142 (3)	0.8472 (3)	0.0492 (7)
H11A	0.3757	1.1081	0.8065	0.059*
C12	0.5248 (3)	0.8915 (3)	0.7937 (3)	0.0475 (7)
H12A	0.5968	0.9031	0.7176	0.057*
C13	0.0370 (3)	1.1306 (3)	1.0983 (3)	0.0421 (6)
H13A	0.0434	1.0412	1.1449	0.051*
C14	−0.1040 (3)	1.2686 (3)	1.1388 (2)	0.0372 (5)
C15	−0.2228 (3)	1.2683 (3)	1.2502 (3)	0.0405 (6)
H15A	−0.2108	1.1795	1.2992	0.049*
C16	−0.3680 (3)	1.5191 (3)	1.2194 (3)	0.0432 (6)
H16A	−0.4579	1.6051	1.2464	0.052*
C17	−0.2541 (3)	1.5289 (3)	1.1081 (3)	0.0456 (6)
H17A	−0.2665	1.6197	1.0622	0.055*
C18	−0.1215 (3)	1.4008 (3)	1.0666 (3)	0.0408 (6)
H18A	−0.0447	1.4036	0.9909	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03204 (13)	0.06102 (16)	0.05624 (16)	−0.01785 (10)	0.01587 (10)	−0.02131 (11)
N1	0.0264 (10)	0.0419 (10)	0.0382 (11)	−0.0094 (9)	0.0035 (8)	−0.0110 (9)
N2	0.0282 (10)	0.0374 (10)	0.0411 (11)	−0.0048 (8)	0.0019 (9)	−0.0082 (9)
N3	0.0340 (11)	0.0366 (10)	0.0471 (12)	−0.0048 (9)	0.0079 (10)	−0.0068 (10)
N4	0.0270 (10)	0.0442 (11)	0.0430 (12)	−0.0088 (9)	0.0045 (9)	−0.0137 (10)
N5	0.0433 (13)	0.0540 (14)	0.0494 (14)	−0.0170 (12)	0.0032 (11)	−0.0059 (12)
O1	0.0671 (18)	0.092 (2)	0.106 (2)	−0.0279 (16)	−0.0287 (17)	0.0307 (18)
O2	0.0651 (16)	0.0626 (14)	0.111 (2)	−0.0149 (12)	−0.0198 (16)	−0.0331 (14)
O3	0.0859 (19)	0.0556 (12)	0.0735 (16)	−0.0326 (13)	−0.0263 (14)	0.0020 (12)
C1	0.0350 (13)	0.0367 (12)	0.0483 (15)	−0.0050 (11)	0.0031 (11)	−0.0087 (11)
C2	0.0443 (16)	0.0356 (12)	0.067 (2)	−0.0132 (12)	0.0051 (14)	−0.0053 (13)
C3	0.0344 (13)	0.0434 (13)	0.0524 (16)	−0.0143 (11)	0.0057 (12)	−0.0025 (12)
C4	0.0253 (11)	0.0378 (11)	0.0317 (11)	−0.0066 (9)	−0.0010 (9)	−0.0074 (10)
C5	0.0282 (11)	0.0388 (12)	0.0369 (12)	−0.0109 (10)	−0.0007 (10)	−0.0091 (10)
C6	0.0268 (11)	0.0417 (12)	0.0390 (13)	−0.0084 (10)	−0.0023 (10)	−0.0123 (11)
C7	0.0240 (11)	0.0386 (12)	0.0380 (12)	−0.0080 (9)	−0.0003 (10)	−0.0071 (10)
C8	0.0297 (12)	0.0362 (12)	0.0475 (15)	−0.0064 (10)	0.0032 (11)	−0.0002 (11)
C9	0.0316 (13)	0.0423 (13)	0.0453 (15)	−0.0056 (11)	0.0096 (11)	−0.0022 (12)
C10	0.0283 (12)	0.0352 (11)	0.0406 (13)	−0.0074 (10)	0.0033 (10)	−0.0073 (10)
C11	0.0411 (14)	0.0357 (12)	0.0488 (16)	−0.0065 (11)	0.0100 (12)	0.0018 (12)
C12	0.0365 (14)	0.0432 (13)	0.0432 (14)	−0.0090 (11)	0.0132 (11)	−0.0034 (12)
C13	0.0336 (13)	0.0327 (11)	0.0468 (14)	−0.0070 (10)	0.0049 (11)	−0.0053 (11)
C14	0.0269 (11)	0.0363 (11)	0.0413 (13)	−0.0084 (10)	0.0016 (10)	−0.0091 (10)
C15	0.0324 (12)	0.0390 (12)	0.0420 (13)	−0.0117 (10)	0.0026 (11)	−0.0044 (11)
C16	0.0290 (12)	0.0416 (13)	0.0487 (15)	−0.0033 (10)	−0.0023 (11)	−0.0127 (12)
C17	0.0398 (14)	0.0408 (13)	0.0461 (15)	−0.0073 (11)	−0.0069 (12)	−0.0004 (12)
C18	0.0319 (12)	0.0431 (13)	0.0391 (13)	−0.0113 (11)	0.0022 (10)	−0.0052 (11)

Geometric parameters (Å, º) top

Ag1—N1	2.162 (2)	C4—C6	1.474 (3)
Ag1—N4ⁱ	2.163 (2)	C5—H5A	0.9300
Ag1—O2	2.731 (3)	C6—H6A	0.9300
Ag1—O3	2.704 (3)	C7—C12	1.378 (4)
Ag1—Ag1ⁱⁱ	3.1631 (8)	C7—C8	1.386 (3)
N1—C1	1.337 (4)	C8—C9	1.382 (3)
N1—C5	1.347 (3)	C8—H8A	0.9300
N2—C6	1.261 (3)	C9—C10	1.385 (4)
N2—C7	1.417 (3)	C9—H9A	0.9300
N3—C13	1.242 (3)	C10—C11	1.381 (4)
N3—C10	1.419 (3)	C11—C12	1.388 (4)
N4—C16	1.336 (4)	C11—H11A	0.9300
N4—C15	1.351 (3)	C12—H12A	0.9300
N5—O1	1.221 (4)	C13—C14	1.472 (3)
N5—O3	1.240 (4)	C13—H13A	0.9300
N5—O2	1.242 (4)	C14—C18	1.382 (4)
C1—C2	1.378 (4)	C14—C15	1.390 (3)
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.379 (4)	C16—C17	1.385 (4)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.385 (4)	C17—C18	1.382 (4)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.382 (3)	C18—H18A	0.9300

N1—Ag1—N4ⁱ	159.44 (9)	C12—C7—C8	119.2 (2)
N1—Ag1—Ag1ⁱⁱ	111.41 (6)	C12—C7—N2	123.7 (2)
N4ⁱ—Ag1—Ag1ⁱⁱ	79.97 (7)	C8—C7—N2	117.0 (2)
N1—Ag1—O2	112.93 (10)	C9—C8—C7	121.0 (2)
N1—Ag1—O3	97.63 (10)	C9—C8—H8A	119.5
N4ⁱ—Ag1—O2	87.07 (9)	C7—C8—H8A	119.5
N4ⁱ—Ag1—O3	92.98 (9)	C8—C9—C10	120.0 (2)
C1—N1—C5	117.7 (2)	C8—C9—H9A	120.0
C1—N1—Ag1	117.05 (16)	C10—C9—H9A	120.0
C5—N1—Ag1	125.13 (18)	C11—C10—C9	118.7 (2)
C6—N2—C7	120.2 (2)	C11—C10—N3	116.5 (2)
C13—N3—C10	121.8 (2)	C9—C10—N3	124.8 (2)
C16—N4—C15	117.8 (2)	C10—C11—C12	121.4 (3)
C16—N4—Ag1ⁱⁱⁱ	122.67 (17)	C10—C11—H11A	119.3
C15—N4—Ag1ⁱⁱⁱ	119.45 (18)	C12—C11—H11A	119.3
O1—N5—O3	119.9 (3)	C7—C12—C11	119.6 (2)
O1—N5—O2	122.2 (3)	C7—C12—H12A	120.2
O3—N5—O2	117.9 (3)	C11—C12—H12A	120.2
N1—C1—C2	122.8 (2)	N3—C13—C14	120.8 (2)
N1—C1—H1A	118.6	N3—C13—H13A	119.6
C2—C1—H1A	118.6	C14—C13—H13A	119.6
C1—C2—C3	119.1 (3)	C18—C14—C15	118.7 (2)
C1—C2—H2A	120.5	C18—C14—C13	120.7 (2)
C3—C2—H2A	120.5	C15—C14—C13	120.7 (2)
C2—C3—C4	119.1 (3)	N4—C15—C14	122.5 (2)
C2—C3—H3A	120.5	N4—C15—H15A	118.8
C4—C3—H3A	120.5	C14—C15—H15A	118.8
C5—C4—C3	118.3 (2)	N4—C16—C17	123.2 (2)
C5—C4—C6	120.4 (2)	N4—C16—H16A	118.4
C3—C4—C6	121.3 (2)	C17—C16—H16A	118.4
N1—C5—C4	123.0 (2)	C18—C17—C16	118.5 (3)
N1—C5—H5A	118.5	C18—C17—H17A	120.7
C4—C5—H5A	118.5	C16—C17—H17A	120.7
N2—C6—C4	120.9 (2)	C14—C18—C17	119.3 (2)
N2—C6—H6A	119.6	C14—C18—H18A	120.3
C4—C6—H6A	119.6	C17—C18—H18A	120.3

Symmetry codes: (i) x+2, y−1, z−1; (ii) −x+3, −y+1, −z+1; (iii) x−2, y+1, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3^iv	0.93	2.50	3.276 (4)	141
C16—H16A···O2^v	0.93	2.44	3.280 (4)	151

Symmetry codes: (iv) −x+3, −y, −z+1; (v) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Ag(NO₃)(C₁₈H₁₄N₄)]
M_r	456.21
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.2148 (18), 9.771 (2), 10.800 (2)
α, β, γ (°)	81.51 (3), 74.27 (3), 66.52 (3)
V (Å³)	857.6 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.31 × 0.30 × 0.08

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.705, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	8493, 3891, 3163
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.094, 1.10
No. of reflections	3891
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.29

Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Selected bond lengths (Å) top

Ag1—N1	2.162 (2)	Ag1—O2	2.731 (3)
Ag1—N4ⁱ	2.163 (2)	Ag1—O3	2.704 (3)

Symmetry code: (i) x+2, y−1, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3ⁱⁱ	0.93	2.50	3.276 (4)	141
C16—H16A···O2ⁱⁱⁱ	0.93	2.44	3.280 (4)	151

Symmetry codes: (ii) −x+3, −y, −z+1; (iii) −x+1, −y+2, −z+2.

Acknowledgements

The authors thank the Natural Science Foundation of Heilongjiang Province (grant No. A200506), the Scientific Research Fund of Heilongjiang Provincial Education Department (grant No. 11553006) and the Doctoral Start-up Fund of Daqing Normal University (grant No. 08ZB02) for supporting this work.

References

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