{6,6′-Dimethoxy-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato-κ4O1,N,N′,O1′}iron(II) monohydrate

Yan, P.-F.; Bao, Y.; Li, H.-F.; Li, G.-M.

doi:10.1107/S1600536809022235

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m832

doi:10.1107/S1600536809022235

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{6,6′-Dimethoxy-2,2′-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato-κ⁴O¹,N,N′,O^1′}iron(II) monohydrate

Peng-Fei Yan,^a Yan Bao,^a Hong-Feng Li ^a and Guang-Ming Li ^a ^*

^aSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: gmli@hlju.edu.cn

(Received 23 May 2009; accepted 11 June 2009; online 27 June 2009)

In the title complex, [Fe(C₂₂H₂₄N₂O₄)]·H₂O, the Fe^II center is four-coordinated by two O and two N atoms from 2,2′-[6,6′-dimethoxycyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolate (L) ligands in a distorted square-planar geometry. Uncoordinated water and FeL molecules are paired via intermolecular water–methoxy O—H⋯O hydrogen bonds.

Related literature

For a manganese complex of a similar Schiff base ligand, see: Watkinson et al. (1999 ). For the isotypic Co^II compound, see: Bao et al. (2009 ).

Experimental

Crystal data

[Fe(C₂₂H₂₄N₂O₄)]·H₂O
M_r = 454.30
Monoclinic, P 2₁ /n
a = 11.243 (5) Å
b = 10.617 (3) Å
c = 17.863 (7) Å
β = 107.042 (14)°
V = 2038.5 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.78 mm⁻¹
T = 291 K
0.22 × 0.21 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.846, T_max = 0.873
18680 measured reflections
4584 independent reflections
3446 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.107
S = 1.03
4584 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H2⋯O2	0.85	2.15	2.915 (4)	149
O5—H1⋯O4	0.85	2.06	2.898 (4)	169

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022235/cv2567sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022235/cv2567Isup2.hkl

checkCIF report

Comment top

In the title compound (Fig. 1), the Fe^II ion is four-coordinated by the tetradentate Schiff base ligand in a square planar environment in a manner observed earlier for a manganese complex (Watkinson et al., 1999). Uncoordinated water molecule is paired with the main molecule by the O—H···O hydrogen bonds (Table 1, Fig. 1).

Related literature top

For a manganese complex of a similar Schiff base ligand, see: Watkinson et al. (1999). For the isotypic Co^II compound, see: Bao et al. (2009).

Experimental top

The title complex was obtained by the treatment of anhydrous ferrous chloride with the Schiff base in methanol/acetone (2:3). The yellow clear mixture turned to black precipitation immediately, stirred for 4 h; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Black single crystals were obtained after several days. Analysis calculated for C₂₂H₂₆Fe_N2_O5: C, 58.16; H, 5.77; N, 6.17; Fe, 12.29; found: C, 57.56; H, 5.23; N, 6.77; F, 12.79%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound showing the atomic numbering and 30% probability displacement ellipsoids. Dashed lines indicate the hydrogen-bonding interactions.

{6,6'-Dimethoxy-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato- κ⁴O¹,N,N',O^1'}iron(II) monohydrate top

Crystal data top

[Fe(C₂₂H₂₄N₂O₄)]·H₂O	F(000) = 952
M_r = 454.30	D_x = 1.480 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 13436 reflections
a = 11.243 (5) Å	θ = 3.1–27.5°
b = 10.617 (3) Å	µ = 0.78 mm⁻¹
c = 17.863 (7) Å	T = 291 K
β = 107.042 (14)°	Block, black
V = 2038.5 (13) Å³	0.22 × 0.21 × 0.18 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4584 independent reflections
Radiation source: fine-focus sealed tube	3446 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.846, T_max = 0.873	k = −13→13
18680 measured reflections	l = −23→23

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0436P)² + 1.092P] where P = (F_o² + 2F_c²)/3
4584 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Fe(C₂₂H₂₄N₂O₄)]·H₂O	V = 2038.5 (13) Å³
M_r = 454.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.243 (5) Å	µ = 0.78 mm⁻¹
b = 10.617 (3) Å	T = 291 K
c = 17.863 (7) Å	0.22 × 0.21 × 0.18 mm
β = 107.042 (14)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4584 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3446 reflections with I > 2σ(I)
T_min = 0.846, T_max = 0.873	R_int = 0.054
18680 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
4584 reflections	Δρ_min = −0.35 e Å⁻³
273 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
Fe1	0.65626 (3)	0.46981 (3)	0.162776 (18)	0.02766 (11)
N1	0.7304 (2)	0.52432 (19)	0.08782 (12)	0.0356 (5)
O1	0.55829 (18)	0.34802 (16)	0.09933 (10)	0.0414 (4)
O3	0.57113 (19)	0.43064 (17)	0.23484 (11)	0.0447 (5)
N2	0.7650 (2)	0.5782 (2)	0.23003 (12)	0.0397 (5)
C7	0.6991 (3)	0.4904 (2)	0.01541 (15)	0.0385 (6)
H7	0.7339	0.5350	−0.0178	0.046*
C1	0.5517 (2)	0.3230 (2)	0.02601 (15)	0.0370 (6)
C2	0.4762 (3)	0.2205 (3)	−0.01171 (17)	0.0439 (6)
C20	0.5684 (3)	0.5024 (2)	0.29420 (15)	0.0401 (6)
O4	0.3917 (2)	0.3866 (2)	0.29798 (13)	0.0597 (6)
C19	0.4729 (3)	0.4826 (3)	0.33048 (17)	0.0481 (7)
O2	0.4206 (2)	0.1564 (2)	0.03582 (13)	0.0636 (6)
C8	0.8176 (3)	0.6325 (2)	0.11520 (15)	0.0394 (6)
H8	0.7676	0.7097	0.1075	0.047*
C14	0.7552 (3)	0.6262 (2)	0.29455 (15)	0.0414 (6)
H14	0.8169	0.6814	0.3220	0.050*
C6	0.6156 (2)	0.3903 (2)	−0.01837 (15)	0.0372 (6)
C4	0.5227 (3)	0.2627 (3)	−0.13222 (17)	0.0517 (7)
H4	0.5117	0.2439	−0.1847	0.062*
C15	0.6547 (3)	0.5989 (3)	0.32603 (15)	0.0421 (6)
C5	0.5980 (3)	0.3603 (3)	−0.09773 (16)	0.0464 (7)
H5	0.6381	0.4075	−0.1269	0.056*
C13	0.8726 (3)	0.6129 (2)	0.20281 (16)	0.0411 (6)
H13	0.9091	0.6918	0.2277	0.049*
C12	0.9700 (3)	0.5089 (3)	0.22201 (18)	0.0502 (7)
H12A	0.9306	0.4287	0.2040	0.060*
H12B	1.0067	0.5038	0.2783	0.060*
C3	0.4622 (3)	0.1911 (3)	−0.08882 (17)	0.0495 (7)
H3	0.4125	0.1234	−0.1121	0.059*
C9	0.9182 (3)	0.6509 (3)	0.07480 (17)	0.0486 (7)
H9A	0.8798	0.6520	0.0186	0.058*
H9B	0.9578	0.7319	0.0899	0.058*
C10	1.0165 (3)	0.5485 (3)	0.09490 (19)	0.0594 (8)
H10A	1.0822	0.5690	0.0719	0.071*
H10B	0.9797	0.4692	0.0727	0.071*
C11	1.0719 (3)	0.5339 (4)	0.1833 (2)	0.0648 (9)
H11A	1.1307	0.4646	0.1943	0.078*
H11B	1.1165	0.6101	0.2049	0.078*
C18	0.4656 (3)	0.5554 (3)	0.3928 (2)	0.0633 (9)
H18	0.4018	0.5412	0.4152	0.076*
C21	0.2942 (3)	0.3601 (4)	0.3316 (2)	0.0694 (10)
H21A	0.3291	0.3303	0.3843	0.104*
H21B	0.2405	0.2967	0.3012	0.104*
H21C	0.2472	0.4354	0.3322	0.104*
C17	0.5525 (4)	0.6499 (3)	0.4229 (2)	0.0674 (10)
H17	0.5468	0.6982	0.4651	0.081*
C16	0.6452 (3)	0.6712 (3)	0.39035 (18)	0.0551 (8)
H16	0.7032	0.7342	0.4106	0.066*
O5	0.3096 (3)	0.3010 (3)	0.13694 (18)	0.1061 (11)
H1	0.3424	0.3299	0.1827	0.159*
H2	0.3649	0.2594	0.1238	0.159*
C22	0.3307 (3)	0.0621 (3)	0.0015 (2)	0.0666 (10)
H22A	0.2609	0.1004	−0.0360	0.100*
H22B	0.3032	0.0219	0.0416	0.100*
H22C	0.3674	0.0005	−0.0243	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02801 (19)	0.03099 (18)	0.02628 (18)	−0.00228 (14)	0.01153 (13)	−0.00086 (13)
N1	0.0334 (12)	0.0387 (11)	0.0353 (11)	−0.0007 (9)	0.0108 (9)	0.0018 (9)
O1	0.0425 (11)	0.0466 (10)	0.0377 (10)	−0.0046 (8)	0.0157 (8)	−0.0025 (7)
O3	0.0515 (12)	0.0491 (10)	0.0391 (10)	−0.0053 (9)	0.0221 (9)	−0.0030 (8)
N2	0.0406 (13)	0.0432 (12)	0.0382 (12)	−0.0011 (10)	0.0163 (10)	−0.0013 (9)
C7	0.0384 (15)	0.0438 (14)	0.0351 (14)	0.0024 (11)	0.0136 (12)	0.0046 (10)
C1	0.0351 (15)	0.0369 (13)	0.0386 (14)	0.0047 (10)	0.0101 (12)	−0.0025 (10)
C2	0.0398 (16)	0.0464 (15)	0.0470 (16)	0.0015 (12)	0.0148 (13)	−0.0043 (12)
C20	0.0409 (16)	0.0498 (15)	0.0318 (13)	0.0055 (11)	0.0141 (12)	0.0041 (10)
O4	0.0513 (14)	0.0833 (15)	0.0531 (13)	−0.0119 (11)	0.0289 (11)	0.0000 (11)
C19	0.0444 (18)	0.0620 (18)	0.0408 (16)	0.0010 (14)	0.0169 (13)	0.0047 (13)
O2	0.0712 (16)	0.0618 (13)	0.0629 (14)	−0.0281 (11)	0.0277 (12)	−0.0130 (10)
C8	0.0363 (15)	0.0393 (14)	0.0432 (15)	−0.0015 (11)	0.0129 (12)	0.0038 (11)
C14	0.0414 (16)	0.0463 (15)	0.0359 (14)	0.0002 (12)	0.0101 (12)	−0.0035 (11)
C6	0.0342 (14)	0.0418 (14)	0.0349 (13)	0.0054 (11)	0.0086 (11)	−0.0004 (10)
C4	0.0539 (19)	0.0608 (18)	0.0390 (16)	0.0104 (14)	0.0112 (14)	−0.0096 (13)
C15	0.0470 (17)	0.0469 (15)	0.0340 (14)	0.0011 (12)	0.0143 (12)	−0.0002 (11)
C5	0.0456 (18)	0.0559 (17)	0.0383 (15)	0.0046 (13)	0.0134 (13)	−0.0003 (12)
C13	0.0387 (16)	0.0445 (14)	0.0417 (15)	−0.0055 (11)	0.0143 (12)	−0.0025 (11)
C12	0.0397 (17)	0.0653 (19)	0.0439 (16)	0.0075 (13)	0.0098 (13)	0.0074 (13)
C3	0.0473 (18)	0.0480 (16)	0.0498 (17)	0.0019 (13)	0.0086 (14)	−0.0111 (13)
C9	0.0451 (18)	0.0587 (18)	0.0440 (16)	−0.0118 (13)	0.0162 (14)	0.0028 (12)
C10	0.0436 (19)	0.085 (2)	0.056 (2)	0.0016 (16)	0.0244 (16)	0.0000 (16)
C11	0.0369 (18)	0.098 (3)	0.061 (2)	0.0095 (17)	0.0161 (15)	0.0101 (18)
C18	0.057 (2)	0.093 (3)	0.0510 (19)	0.0029 (18)	0.0322 (17)	−0.0024 (16)
C21	0.046 (2)	0.106 (3)	0.065 (2)	−0.0016 (19)	0.0290 (17)	0.0186 (19)
C17	0.077 (3)	0.084 (2)	0.051 (2)	−0.001 (2)	0.0337 (19)	−0.0176 (17)
C16	0.062 (2)	0.0628 (19)	0.0436 (17)	0.0018 (15)	0.0206 (15)	−0.0097 (13)
O5	0.080 (2)	0.167 (3)	0.080 (2)	−0.021 (2)	0.0366 (17)	−0.0236 (19)
C22	0.055 (2)	0.0543 (19)	0.085 (3)	−0.0180 (15)	0.0124 (19)	−0.0009 (16)

Geometric parameters (Å, º) top

Fe1—N2	1.844 (2)	C4—H4	0.9300
Fe1—O1	1.8541 (18)	C15—C16	1.412 (4)
Fe1—O3	1.8623 (19)	C5—H5	0.9300
Fe1—N1	1.864 (2)	C13—C12	1.523 (4)
N1—C7	1.288 (3)	C13—H13	0.9800
N1—C8	1.496 (3)	C12—C11	1.525 (4)
O1—C1	1.317 (3)	C12—H12A	0.9700
O3—C20	1.313 (3)	C12—H12B	0.9700
N2—C14	1.294 (3)	C3—H3	0.9300
N2—C13	1.476 (3)	C9—C10	1.517 (4)
C7—C6	1.429 (4)	C9—H9A	0.9700
C7—H7	0.9300	C9—H9B	0.9700
C1—C6	1.410 (4)	C10—C11	1.525 (5)
C1—C2	1.423 (4)	C10—H10A	0.9700
C2—O2	1.373 (3)	C10—H10B	0.9700
C2—C3	1.376 (4)	C11—H11A	0.9700
C20—C15	1.411 (4)	C11—H11B	0.9700
C20—C19	1.424 (4)	C18—C17	1.394 (5)
O4—C19	1.378 (4)	C18—H18	0.9300
O4—C21	1.425 (4)	C21—H21A	0.9600
C19—C18	1.377 (4)	C21—H21B	0.9600
O2—C22	1.428 (4)	C21—H21C	0.9600
C8—C13	1.519 (4)	C17—C16	1.352 (5)
C8—C9	1.522 (4)	C17—H17	0.9300
C8—H8	0.9800	C16—H16	0.9300
C14—C15	1.431 (4)	O5—H1	0.8500
C14—H14	0.9300	O5—H2	0.8500
C6—C5	1.409 (4)	C22—H22A	0.9600
C4—C5	1.365 (4)	C22—H22B	0.9600
C4—C3	1.397 (4)	C22—H22C	0.9600

N2—Fe1—O1	174.23 (9)	C8—C13—C12	112.4 (2)
N2—Fe1—O3	93.78 (9)	N2—C13—H13	109.8
O1—Fe1—O3	86.17 (8)	C8—C13—H13	109.8
N2—Fe1—N1	85.62 (10)	C12—C13—H13	109.8
O1—Fe1—N1	95.05 (9)	C13—C12—C11	111.0 (2)
O3—Fe1—N1	173.78 (9)	C13—C12—H12A	109.4
C7—N1—C8	120.2 (2)	C11—C12—H12A	109.4
C7—N1—Fe1	125.91 (19)	C13—C12—H12B	109.4
C8—N1—Fe1	113.05 (16)	C11—C12—H12B	109.4
C1—O1—Fe1	126.75 (17)	H12A—C12—H12B	108.0
C20—O3—Fe1	124.53 (17)	C2—C3—C4	120.0 (3)
C14—N2—C13	119.1 (2)	C2—C3—H3	120.0
C14—N2—Fe1	127.8 (2)	C4—C3—H3	120.0
C13—N2—Fe1	113.07 (16)	C10—C9—C8	112.8 (2)
N1—C7—C6	125.7 (2)	C10—C9—H9A	109.0
N1—C7—H7	117.1	C8—C9—H9A	109.0
C6—C7—H7	117.1	C10—C9—H9B	109.0
O1—C1—C6	124.6 (2)	C8—C9—H9B	109.0
O1—C1—C2	118.5 (2)	H9A—C9—H9B	107.8
C6—C1—C2	116.9 (2)	C9—C10—C11	111.5 (3)
O2—C2—C3	124.5 (3)	C9—C10—H10A	109.3
O2—C2—C1	113.8 (2)	C11—C10—H10A	109.3
C3—C2—C1	121.7 (3)	C9—C10—H10B	109.3
O3—C20—C15	124.8 (3)	C11—C10—H10B	109.3
O3—C20—C19	118.8 (3)	H10A—C10—H10B	108.0
C15—C20—C19	116.4 (2)	C12—C11—C10	110.7 (3)
C19—O4—C21	117.7 (3)	C12—C11—H11A	109.5
C18—C19—O4	124.5 (3)	C10—C11—H11A	109.5
C18—C19—C20	121.2 (3)	C12—C11—H11B	109.5
O4—C19—C20	114.3 (2)	C10—C11—H11B	109.5
C2—O2—C22	118.4 (3)	H11A—C11—H11B	108.1
N1—C8—C13	105.1 (2)	C19—C18—C17	120.9 (3)
N1—C8—C9	116.7 (2)	C19—C18—H18	119.6
C13—C8—C9	111.8 (2)	C17—C18—H18	119.6
N1—C8—H8	107.6	O4—C21—H21A	109.5
C13—C8—H8	107.6	O4—C21—H21B	109.5
C9—C8—H8	107.6	H21A—C21—H21B	109.5
N2—C14—C15	123.6 (3)	O4—C21—H21C	109.5
N2—C14—H14	118.2	H21A—C21—H21C	109.5
C15—C14—H14	118.2	H21B—C21—H21C	109.5
C5—C6—C1	120.4 (2)	C16—C17—C18	119.8 (3)
C5—C6—C7	118.3 (2)	C16—C17—H17	120.1
C1—C6—C7	121.3 (2)	C18—C17—H17	120.1
C5—C4—C3	120.1 (3)	C17—C16—C15	120.7 (3)
C5—C4—H4	120.0	C17—C16—H16	119.6
C3—C4—H4	120.0	C15—C16—H16	119.6
C20—C15—C16	121.0 (3)	H1—O5—H2	107.8
C20—C15—C14	121.1 (2)	O2—C22—H22A	109.5
C16—C15—C14	117.8 (3)	O2—C22—H22B	109.5
C4—C5—C6	120.8 (3)	H22A—C22—H22B	109.5
C4—C5—H5	119.6	O2—C22—H22C	109.5
C6—C5—H5	119.6	H22A—C22—H22C	109.5
N2—C13—C8	104.4 (2)	H22B—C22—H22C	109.5
N2—C13—C12	110.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H2···O1	0.85	2.52	3.102 (4)	126
O5—H2···O2	0.85	2.15	2.915 (4)	149
O5—H1···O3	0.85	2.69	3.254 (4)	125
O5—H1···O4	0.85	2.06	2.898 (4)	169

Experimental details

Crystal data
Chemical formula	[Fe(C₂₂H₂₄N₂O₄)]·H₂O
M_r	454.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	11.243 (5), 10.617 (3), 17.863 (7)
β (°)	107.042 (14)
V (Å³)	2038.5 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.22 × 0.21 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.846, 0.873
No. of measured, independent and observed [I > 2σ(I)] reflections	18680, 4584, 3446
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.107, 1.03
No. of reflections	4584
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.35

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), 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
O5—H2···O2	0.85	2.15	2.915 (4)	149.1
O5—H1···O4	0.85	2.06	2.898 (4)	169.0

Acknowledgements

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20572018 and 20672032), Heilongjiang Province (grant Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University.

References

Bao, Y., Li, H.-F., Yan, P.-F. Li, G.-M. & Hou, G.-F. (2009). Acta Cryst. E65, m770. Web of Science CSD CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-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
Watkinson, M., Fondo, M., Bermejo, M. R., Sousa, A., McAuliffe, C. A., Pritchard, R. G., Jaiboon, N., Aurangzeb, N. & Naeem, M. (1999). J. Chem. Soc. Dalton Trans. pp. 31–41. Web of Science CSD CrossRef Google Scholar

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