catena-Poly[[bis­(2,4-dichloro­benzoato)bis­(methanol-κO)cobalt(II)]-μ-4,4′-bipyridine-κ2N:N′]

Hyun, M.Y.; Kim, P.-G.; Kim, C.; Kim, Y.

doi:10.1107/S1600536811046149

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1705

https://doi.org/10.1107/S1600536811046149

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catena-Poly[[bis(2,4-dichlorobenzoato)bis(methanol-κO)cobalt(II)]-μ-4,4′-bipyridine-κ²N:N′]

Min Young Hyun,^a Pan-Gi Kim,^b Cheal Kim ^a ^* and Youngmee Kim ^c ^*

^aDepartment of Fine Chemistry, Seoul National University of Science and Technology, Seoul 139-743, Republic of Korea, ^bDepartment of Forest & Environment Resources, Kyungpook National University, Sangju 742-711, Republic of Korea, and ^cDepartment of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea
^*Correspondence e-mail: chealkim@seoultech.ac.kr, ymeekim@ewha.ac.kr

(Received 27 October 2011; accepted 2 November 2011; online 9 November 2011)

In the title compound, [Co(C₇H₃Cl₂O₂)₂(C₁₀H₈N₂)(CH₃OH)₂]_n, the Co^II ion lies on a twofold rotation axis and is in a slightly distorted octahedral CdO₄N₂ environment, formed by two O atoms from monodentate dichlorobenzoate ligands, two O atoms from methanol ligands, and two N atoms from trans-related 4,4′-bipyridine ligands. The bipyridine ligands also lies on a twofold rotation axis and bridge the Co^II ions, forming chains extending along [010]. An intrachain O—H⋯O hydrogen bond is observed.

Related literature

For interactions of metal ions with amino acids, see: Stoumpos et al. (2009 ). For related complexes, see: Yu et al. (2010 ); Hyun et al. (2011 ); Kang et al. (2011 ); Kim et al. (2011 ); Song et al. (2009 ).

Experimental

Crystal data

[Co(C₇H₃Cl₂O₂)₂(C₁₀H₈N₂)(CH₄O)₂]
M_r = 659.19
Monoclinic, C 2/c
a = 20.8405 (16) Å
b = 11.4228 (9) Å
c = 15.0728 (12) Å
β = 127.479 (1)°
V = 2847.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 288 K
0.10 × 0.08 × 0.03 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.907, T_max = 0.970
7806 measured reflections
2801 independent reflections
2178 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.092
S = 1.06
2801 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2ⁱ	0.70 (3)	1.96 (3)	2.625 (2)	160 (3)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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: https://doi.org/10.1107/S1600536811046149/lh5365sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046149/lh5365Isup2.hkl

checkCIF report

Comment top

The interaction of transition metal ions with biologically active molecules such as amino acids and various acids in the biological systems is of great importance (Stoumpos, et al., 2009). Therefore, we and other groups have intensively examined the interaction of transition metal ions with various acids such as benzoic acid and acetic acid. As a result, there are a variety of structures in the literature of copper(II), cadmium(II), nickel(II), and zinc(II) benzoates with quinoxaline, 6-methylquinoline, 3-methylquinoline, trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene, and di-2-pyridyl ketone (Yu, et al., 2010; Hyun, et al., 2011; Kang, et al., 2011; Kim, et al., 2011). Nevertheless, cobalt as a metal ion source has rarely been used (Song, et al., 2009). In this work, we have employed cobalt(II) benzoate as a building block and 4,4'-bipyridine as a ligand. We report herein the crystal structure of the title compound.

In the title compound, the Co^II ion lies on a two-fold rotation axis and is in a distorted octahedral CdO₄N₂ environment, constructed by two O atoms from dichlorobenzoate ligands, two O atoms from methanol ligands, and two N atoms from the trans-related 4,4'-bipyridine, which also lies on a two-fold rotation axis (Fig. 1). The 4,4'-bipyridine ligands bridge the Co^II complex units, forming chains extending along the [010] direction.

Related literature top

For interactions of metal ions with amino acids, see: Stoumpos et al. (2009). For related complexes, see: Yu et al. (2010); Hyun et al. (2011); Kang et al. (2011); Kim et al. (2011); Song et al. (2009).

Experimental top

2,4-Dichlorobenzoic acid (19.1 mg, 0.1 mmol), NH₄OH (13.9 ml, 0.1 mmol) and Co(NO₃)2.6H2O (14.6 mg, 0.05 mmol) were dissolved in 4 ml methanol and carefully layered with a 4 ml methylene chloride solution of 4,4'-bipyridine (15.6 mg, 0.1 mmol). Suitable crystals of the title compound were obtained in a month.

Structure description top

For interactions of metal ions with amino acids, see: Stoumpos et al. (2009). For related complexes, see: Yu et al. (2010); Hyun et al. (2011); Kang et al. (2011); Kim et al. (2011); Song et al. (2009).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. A fragment of the one-dimensional chain structure of the title compound showing displacement ellipsoids at the 30% probability level. Unlabeled atoms are related by the symmetry operator (-x, y, 0.5 - z).

catena-Poly[[bis(2,4-dichlorobenzoato)bis(methanol- κO)cobalt(II)]-µ-4,4'-bipyridine-κ²N:N'] top

Crystal data top

[Co(C₇H₃Cl₂O₂)₂(C₁₀H₈N₂)(CH₄O)₂]	F(000) = 1340
M_r = 659.19	D_x = 1.538 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2248 reflections
a = 20.8405 (16) Å	θ = 2.3–25.2°
b = 11.4228 (9) Å	µ = 1.02 mm⁻¹
c = 15.0728 (12) Å	T = 288 K
β = 127.479 (1)°	Plate, orange
V = 2847.5 (4) Å³	0.10 × 0.08 × 0.03 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2801 independent reflections
Radiation source: fine-focus sealed tube	2178 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −25→18
T_min = 0.907, T_max = 0.970	k = −11→14
7806 measured reflections	l = −18→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0539P)² + 0.195P] where P = (F_o² + 2F_c²)/3
2801 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Co(C₇H₃Cl₂O₂)₂(C₁₀H₈N₂)(CH₄O)₂]	V = 2847.5 (4) Å³
M_r = 659.19	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 20.8405 (16) Å	µ = 1.02 mm⁻¹
b = 11.4228 (9) Å	T = 288 K
c = 15.0728 (12) Å	0.10 × 0.08 × 0.03 mm
β = 127.479 (1)°

Data collection top

Bruker SMART CCD diffractometer	2801 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2178 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.970	R_int = 0.026
7806 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.46 e Å⁻³
2801 reflections	Δρ_min = −0.45 e Å⁻³
184 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
Co1	0.0000	0.25358 (3)	0.2500	0.03212 (14)
Cl1	0.14268 (5)	0.07781 (6)	0.63891 (6)	0.0674 (2)
Cl2	0.27648 (5)	0.39785 (8)	0.96582 (5)	0.0778 (3)
N11	0.0000	0.06476 (19)	0.2500	0.0357 (6)
N12	0.0000	0.44441 (19)	0.2500	0.0348 (5)
O1	0.06270 (9)	0.25755 (11)	0.42246 (12)	0.0390 (4)
O2	−0.03520 (12)	0.28061 (19)	0.44020 (14)	0.0718 (6)
O3	0.11240 (11)	0.25907 (14)	0.27604 (15)	0.0460 (4)
H3O	0.1016 (17)	0.262 (2)	0.222 (2)	0.051 (9)*
C1	0.03654 (15)	0.27797 (18)	0.47722 (18)	0.0402 (5)
C2	0.09941 (13)	0.30634 (19)	0.60010 (16)	0.0371 (5)
C3	0.14937 (15)	0.2225 (2)	0.67935 (19)	0.0435 (5)
C4	0.20443 (15)	0.2499 (2)	0.79167 (19)	0.0510 (6)
H4	0.2371	0.1923	0.8439	0.061*
C5	0.20962 (14)	0.3633 (2)	0.82401 (18)	0.0484 (6)
C6	0.16244 (15)	0.4504 (2)	0.74806 (19)	0.0485 (6)
H6	0.1674	0.5274	0.7714	0.058*
C7	0.10782 (15)	0.42101 (19)	0.63699 (18)	0.0444 (5)
H7	0.0757	0.4793	0.5852	0.053*
C11	0.01623 (14)	0.00268 (18)	0.33700 (17)	0.0405 (5)
H11	0.0275	0.0434	0.3985	0.049*
C12	0.01723 (14)	−0.11759 (17)	0.34075 (17)	0.0376 (5)
H12	0.0293	−0.1563	0.4036	0.045*
C13	0.0000	−0.1806 (2)	0.2500	0.0310 (6)
C14	0.0000	0.6896 (2)	0.2500	0.0315 (6)
C15	0.05524 (13)	0.62607 (17)	0.34646 (17)	0.0373 (5)
H15	0.0929	0.6646	0.4135	0.045*
C16	0.05389 (14)	0.50533 (17)	0.34212 (17)	0.0371 (5)
H16	0.0926	0.4643	0.4069	0.045*
C31	0.17939 (16)	0.1836 (3)	0.3450 (2)	0.0693 (8)
H31A	0.1901	0.1756	0.4163	0.104*
H31B	0.2260	0.2159	0.3553	0.104*
H31C	0.1675	0.1081	0.3101	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0505 (3)	0.0178 (2)	0.0336 (2)	0.000	0.0284 (2)	0.000
Cl1	0.0934 (6)	0.0445 (4)	0.0610 (4)	0.0235 (3)	0.0453 (4)	0.0071 (3)
Cl2	0.0728 (5)	0.0986 (6)	0.0369 (3)	−0.0283 (4)	0.0205 (3)	−0.0094 (3)
N11	0.0521 (16)	0.0194 (11)	0.0377 (13)	0.000	0.0284 (12)	0.000
N12	0.0500 (15)	0.0205 (11)	0.0388 (13)	0.000	0.0297 (13)	0.000
O1	0.0572 (10)	0.0299 (8)	0.0362 (8)	0.0037 (6)	0.0316 (8)	0.0000 (6)
O2	0.0524 (12)	0.1249 (18)	0.0406 (9)	−0.0081 (11)	0.0295 (9)	−0.0142 (10)
O3	0.0547 (11)	0.0452 (10)	0.0403 (9)	0.0037 (7)	0.0300 (9)	0.0038 (8)
C1	0.0570 (15)	0.0313 (11)	0.0366 (11)	0.0005 (10)	0.0307 (11)	0.0008 (9)
C2	0.0437 (13)	0.0391 (12)	0.0339 (11)	0.0010 (9)	0.0264 (10)	0.0003 (9)
C3	0.0518 (14)	0.0432 (13)	0.0419 (12)	0.0055 (10)	0.0318 (12)	0.0015 (10)
C4	0.0486 (14)	0.0614 (17)	0.0392 (12)	0.0100 (12)	0.0248 (12)	0.0124 (11)
C5	0.0432 (13)	0.0651 (17)	0.0337 (11)	−0.0109 (12)	0.0218 (11)	−0.0053 (11)
C6	0.0557 (15)	0.0466 (14)	0.0466 (13)	−0.0100 (11)	0.0328 (13)	−0.0094 (11)
C7	0.0527 (14)	0.0390 (13)	0.0375 (11)	0.0002 (10)	0.0254 (11)	0.0000 (10)
C11	0.0641 (15)	0.0230 (10)	0.0391 (11)	−0.0017 (10)	0.0339 (11)	−0.0033 (8)
C12	0.0562 (14)	0.0230 (10)	0.0380 (11)	−0.0015 (9)	0.0310 (11)	0.0021 (8)
C13	0.0333 (16)	0.0207 (14)	0.0385 (15)	0.000	0.0216 (14)	0.000
C14	0.0419 (17)	0.0203 (14)	0.0406 (15)	0.000	0.0294 (14)	0.000
C15	0.0468 (13)	0.0254 (10)	0.0363 (11)	−0.0033 (9)	0.0235 (11)	−0.0022 (8)
C16	0.0470 (13)	0.0236 (10)	0.0385 (11)	0.0027 (9)	0.0249 (11)	0.0041 (9)
C31	0.0593 (18)	0.074 (2)	0.0657 (18)	0.0147 (15)	0.0335 (16)	0.0082 (15)

Geometric parameters (Å, º) top

Co1—O1	2.0816 (14)	C4—H4	0.9300
Co1—O1ⁱ	2.0816 (14)	C5—C6	1.377 (3)
Co1—O3ⁱ	2.1274 (18)	C6—C7	1.375 (3)
Co1—O3	2.1275 (18)	C6—H6	0.9300
Co1—N11	2.157 (2)	C7—H7	0.9300
Co1—N12	2.180 (2)	C11—C12	1.375 (3)
Cl1—C3	1.738 (2)	C11—H11	0.9300
Cl2—C5	1.744 (2)	C12—C13	1.386 (2)
N11—C11	1.341 (2)	C12—H12	0.9300
N11—C11ⁱ	1.341 (2)	C13—C12ⁱ	1.386 (2)
N12—C16ⁱ	1.333 (2)	C13—C14ⁱⁱ	1.484 (4)
N12—C16	1.333 (2)	C14—C15	1.389 (2)
O1—C1	1.257 (3)	C14—C15ⁱ	1.389 (2)
O2—C1	1.238 (3)	C14—C13ⁱⁱⁱ	1.484 (4)
O3—C31	1.417 (3)	C15—C16	1.380 (3)
O3—H3O	0.70 (3)	C15—H15	0.9300
C1—C2	1.516 (3)	C16—H16	0.9300
C2—C3	1.384 (3)	C31—H31A	0.9600
C2—C7	1.392 (3)	C31—H31B	0.9600
C3—C4	1.384 (3)	C31—H31C	0.9600
C4—C5	1.366 (3)

O1—Co1—O1ⁱ	177.51 (7)	C5—C4—H4	120.7
O1—Co1—O3ⁱ	90.79 (6)	C3—C4—H4	120.7
O1ⁱ—Co1—O3ⁱ	89.13 (6)	C4—C5—C6	121.8 (2)
O1—Co1—O3	89.13 (6)	C4—C5—Cl2	118.86 (19)
O1ⁱ—Co1—O3	90.79 (6)	C6—C5—Cl2	119.32 (19)
O3ⁱ—Co1—O3	176.63 (9)	C7—C6—C5	118.7 (2)
O1—Co1—N11	91.25 (4)	C7—C6—H6	120.7
O1ⁱ—Co1—N11	91.25 (4)	C5—C6—H6	120.7
O3ⁱ—Co1—N11	91.69 (4)	C6—C7—C2	121.7 (2)
O3—Co1—N11	91.69 (4)	C6—C7—H7	119.2
O1—Co1—N12	88.75 (4)	C2—C7—H7	119.2
O1ⁱ—Co1—N12	88.75 (4)	N11—C11—C12	123.88 (19)
O3ⁱ—Co1—N12	88.31 (4)	N11—C11—H11	118.1
O3—Co1—N12	88.31 (4)	C12—C11—H11	118.1
N11—Co1—N12	180.0	C11—C12—C13	119.34 (19)
C11—N11—C11ⁱ	116.1 (2)	C11—C12—H12	120.3
C11—N11—Co1	121.94 (12)	C13—C12—H12	120.3
C11ⁱ—N11—Co1	121.94 (12)	C12—C13—C12ⁱ	117.4 (2)
C16ⁱ—N12—C16	117.0 (2)	C12—C13—C14ⁱⁱ	121.28 (12)
C16ⁱ—N12—Co1	121.47 (12)	C12ⁱ—C13—C14ⁱⁱ	121.28 (12)
C16—N12—Co1	121.48 (12)	C15—C14—C15ⁱ	117.0 (2)
C1—O1—Co1	129.08 (15)	C15—C14—C13ⁱⁱⁱ	121.48 (12)
C31—O3—Co1	126.90 (17)	C15ⁱ—C14—C13ⁱⁱⁱ	121.48 (12)
C31—O3—H3O	111 (2)	C16—C15—C14	119.49 (19)
Co1—O3—H3O	104 (2)	C16—C15—H15	120.3
O2—C1—O1	126.6 (2)	C14—C15—H15	120.3
O2—C1—C2	117.03 (19)	N12—C16—C15	123.4 (2)
O1—C1—C2	116.4 (2)	N12—C16—H16	118.3
C3—C2—C7	117.4 (2)	C15—C16—H16	118.3
C3—C2—C1	122.9 (2)	O3—C31—H31A	109.5
C7—C2—C1	119.63 (19)	O3—C31—H31B	109.5
C2—C3—C4	121.9 (2)	H31A—C31—H31B	109.5
C2—C3—Cl1	119.86 (18)	O3—C31—H31C	109.5
C4—C3—Cl1	118.28 (18)	H31A—C31—H31C	109.5
C5—C4—C3	118.5 (2)	H31B—C31—H31C	109.5

O1—Co1—N11—C11	16.24 (13)	O1—C1—C2—C3	−74.4 (3)
O1ⁱ—Co1—N11—C11	−163.76 (13)	O2—C1—C2—C7	−71.7 (3)
O3ⁱ—Co1—N11—C11	−74.59 (13)	O1—C1—C2—C7	106.2 (2)
O3—Co1—N11—C11	105.41 (13)	C7—C2—C3—C4	1.6 (3)
O1—Co1—N11—C11ⁱ	−163.75 (13)	C1—C2—C3—C4	−177.7 (2)
O1ⁱ—Co1—N11—C11ⁱ	16.24 (13)	C7—C2—C3—Cl1	−179.46 (17)
O3ⁱ—Co1—N11—C11ⁱ	105.41 (13)	C1—C2—C3—Cl1	1.2 (3)
O3—Co1—N11—C11ⁱ	−74.58 (13)	C2—C3—C4—C5	−0.7 (4)
O1—Co1—N12—C16ⁱ	−158.24 (11)	Cl1—C3—C4—C5	−179.63 (19)
O1ⁱ—Co1—N12—C16ⁱ	21.76 (11)	C3—C4—C5—C6	−0.7 (4)
O3ⁱ—Co1—N12—C16ⁱ	−67.41 (12)	C3—C4—C5—Cl2	177.98 (18)
O3—Co1—N12—C16ⁱ	112.59 (12)	C4—C5—C6—C7	1.1 (4)
O1—Co1—N12—C16	21.76 (11)	Cl2—C5—C6—C7	−177.58 (18)
O1ⁱ—Co1—N12—C16	−158.24 (11)	C5—C6—C7—C2	−0.1 (4)
O3ⁱ—Co1—N12—C16	112.59 (12)	C3—C2—C7—C6	−1.2 (3)
O3—Co1—N12—C16	−67.41 (12)	C1—C2—C7—C6	178.2 (2)
O3ⁱ—Co1—O1—C1	−11.09 (17)	C11ⁱ—N11—C11—C12	0.28 (17)
O3—Co1—O1—C1	165.54 (17)	Co1—N11—C11—C12	−179.71 (17)
N11—Co1—O1—C1	−102.79 (16)	N11—C11—C12—C13	−0.6 (3)
N12—Co1—O1—C1	77.21 (16)	C11—C12—C13—C12ⁱ	0.27 (16)
O1—Co1—O3—C31	52.8 (2)	C11—C12—C13—C14ⁱⁱ	−179.74 (16)
O1ⁱ—Co1—O3—C31	−129.7 (2)	C15ⁱ—C14—C15—C16	1.09 (14)
N11—Co1—O3—C31	−38.4 (2)	C13ⁱⁱⁱ—C14—C15—C16	−178.90 (14)
N12—Co1—O3—C31	141.6 (2)	C16ⁱ—N12—C16—C15	1.19 (15)
Co1—O1—C1—O2	13.4 (3)	Co1—N12—C16—C15	−178.81 (15)
Co1—O1—C1—C2	−164.25 (13)	C14—C15—C16—N12	−2.4 (3)
O2—C1—C2—C3	107.7 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2ⁱ	0.70 (3)	1.96 (3)	2.625 (2)	160 (3)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₇H₃Cl₂O₂)₂(C₁₀H₈N₂)(CH₄O)₂]
M_r	659.19
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	288
a, b, c (Å)	20.8405 (16), 11.4228 (9), 15.0728 (12)
β (°)	127.479 (1)
V (Å³)	2847.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.10 × 0.08 × 0.03

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.907, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	7806, 2801, 2178
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.092, 1.06
No. of reflections	2801
No. of parameters	184
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.45

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2ⁱ	0.70 (3)	1.96 (3)	2.625 (2)	160 (3)

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

Financial support from the Forest Science & Technology Projects (S121011L080120) and the Cooperative Research Program for Agricultural Science & Technology Development (20070301–036-019–02) is gratefully acknowledged.

References

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