PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m5.
Published online 2009 December 4. doi:  10.1107/S1600536809051563
PMCID: PMC2980000

Aqua­bis(2,3-dimethyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-olato)nickel(II)

Abstract

In the crystal structure of the mononuclear title complex, [Ni(C10H9N2O2)2(H2O)], the NiII ion is five-coordinated in a distorted square-pyramidal geometry by two N atoms and two O atoms from 2,3-dimethyl-4-oxopyrido[1,2-a]pyrimidin-9-olate ligands and one O atom from a water mol­ecule. O—H(...)O hydrogen bonds between the coordinated water mol­ecule and the ligand connect adjacent mol­ecules, forming a ribbon parallel to the b axis.

Related literature

For the design and synthesis of self-assembling systems with organic ligands containing N and O donors, see: Wei et al. (2009 [triangle]); Sun et al. (2008 [triangle]); Bayot et al. (2006 [triangle]); Chen et al. (2007 [triangle]). For structures of quinolin-8-ol complexes, see: Wu et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-000m5-scheme1.jpg

Experimental

Crystal data

  • [Ni(C10H9N2O2)2(H2O)]
  • M r = 455.11
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-000m5-efi1.jpg
  • a = 13.4032 (14) Å
  • b = 12.1313 (12) Å
  • c = 12.4631 (11) Å
  • β = 99.386 (1)°
  • V = 1999.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.01 mm−1
  • T = 298 K
  • 0.30 × 0.20 × 0.12 mm

Data collection

  • Rigaku SCXmini CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.751, T max = 0.888
  • 10283 measured reflections
  • 3520 independent reflections
  • 2242 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.132
  • S = 1.03
  • 3520 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809051563/zq2018sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051563/zq2018Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Considerable attention has been paid to the design and synthesis of complexes with organic ligands containing N and O donors (Wei et al., 2009; Sun et al., 2008; Bayot et al., 2006; Chen, et al., 2007). Quinolin-8-ol is one such ligand and several crystal structures of complexes containing it have been reported (Wu et al., 2006). We report here the synthesis and crystal structure of the title complex (I) (Fig. 1). In (I), the Ni atom is five-coordinated by two pyridine nitrogen atoms and two oxygen atoms from the hydroxy groups and one oxygen atom from a water molecule (Fig. 1). Intermolecular O—H···O hydrogen bonds (Fig.2 and Table 1) connecting the molecules of (I) define the crystal packing.

Experimental

All chemicals used (reagent grade) were commercially available. An aqueous solution (5 ml) of Ni(Ac)2.4H2O (24.9 mg, 0.1 mmol) was added to an ethanol solution (10 ml) containing 2,3-dimethyl-9-hydroxylpyrido[1,2-a]pyrimidin-4-one (38.0 mg, 0.2 mmol) then filtered off. The resulting solution was continuously stirred for about 30 min and then filtered. The filtrate was slowly evaporated at room temperature over several days and colorless prism crystals suitable for X-ray analysis were obtained.

Refinement

The H atoms bound to carbon were placed in geometrical positions and refined using a riding model, with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, and with C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The H atoms of the coordinated water were located from the Fourier difference map and refined with a distance restraint of O–H = 0.85 Å.

Figures

Fig. 1.
The molecular structure of the title molecule and the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Crystal packing of compound (I). Hydrogen bonds are shown as dashed lines.

Crystal data

[Ni(C10H9N2O2)2(H2O)]F(000) = 944
Mr = 455.11Dx = 1.512 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2294 reflections
a = 13.4032 (14) Åθ = 2.3–23.7°
b = 12.1313 (12) ŵ = 1.01 mm1
c = 12.4631 (11) ÅT = 298 K
β = 99.386 (1)°Prism, colorless
V = 1999.3 (3) Å30.30 × 0.20 × 0.12 mm
Z = 4

Data collection

Rigaku SCXmini CCD area-detector diffractometer3520 independent reflections
Radiation source: fine-focus sealed tube2242 reflections with I > 2σ(I)
graphiteRint = 0.045
phi and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 200)h = −15→15
Tmin = 0.751, Tmax = 0.888k = −13→14
10283 measured reflectionsl = −8→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0496P)2 + 2.7285P] where P = (Fo2 + 2Fc2)/3
3520 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.40 e Å3

Special details

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)

xyzUiso*/Ueq
Ni10.79535 (4)0.41721 (5)0.19800 (5)0.0428 (2)
N10.6831 (2)0.4337 (3)0.0534 (3)0.0351 (9)
N20.5489 (3)0.3281 (3)−0.0425 (3)0.0413 (10)
N30.9220 (2)0.3915 (3)0.3261 (3)0.0334 (8)
N41.0960 (3)0.4366 (3)0.3602 (3)0.0348 (9)
O10.7277 (2)0.2737 (3)0.1993 (2)0.0460 (8)
O20.4536 (3)0.3929 (3)−0.1970 (3)0.0690 (12)
O30.9049 (2)0.4701 (3)0.1247 (2)0.0460 (8)
O41.1941 (2)0.3960 (3)0.5228 (3)0.0536 (9)
O50.7303 (2)0.5312 (3)0.2785 (3)0.0679 (11)
H5A0.66970.55140.25620.082*
H5B0.75500.56740.33500.082*
C10.6639 (3)0.5152 (4)−0.0221 (4)0.0404 (11)
C20.5870 (4)0.5058 (4)−0.1098 (4)0.0475 (13)
C30.5254 (3)0.4119 (5)−0.1233 (4)0.0479 (13)
C40.6274 (3)0.3425 (4)0.0416 (3)0.0337 (10)
C50.6514 (3)0.2575 (4)0.1225 (4)0.0373 (11)
C60.5915 (4)0.1653 (4)0.1126 (4)0.0504 (13)
H60.60500.10890.16340.061*
C70.5104 (4)0.1549 (5)0.0275 (5)0.0621 (15)
H70.47000.09220.02310.075*
C80.4899 (4)0.2337 (5)−0.0480 (5)0.0586 (15)
H80.43580.2252−0.10450.070*
C90.7298 (4)0.6146 (4)−0.0027 (4)0.0582 (14)
H9A0.76610.61300.07030.087*
H9B0.68870.6798−0.01300.087*
H9C0.77690.6149−0.05300.087*
C100.5654 (4)0.5939 (5)−0.1961 (4)0.0653 (16)
H10A0.56960.6652−0.16220.098*
H10B0.49870.5834−0.23650.098*
H10C0.61420.5891−0.24450.098*
C110.9307 (3)0.3468 (4)0.4274 (3)0.0352 (10)
C121.0208 (3)0.3451 (4)0.4981 (3)0.0362 (10)
C131.1084 (3)0.3907 (4)0.4675 (4)0.0378 (11)
C141.0038 (3)0.4335 (3)0.2942 (3)0.0311 (10)
C150.9932 (3)0.4783 (4)0.1855 (3)0.0360 (10)
C161.0767 (4)0.5258 (4)0.1534 (4)0.0466 (12)
H161.07210.55580.08410.056*
C171.1679 (4)0.5290 (4)0.2247 (4)0.0527 (13)
H171.22340.56230.20210.063*
C181.1788 (3)0.4855 (4)0.3254 (4)0.0480 (13)
H181.24100.48830.37110.058*
C190.8349 (3)0.3004 (4)0.4571 (4)0.0484 (13)
H19A0.81310.34560.51210.073*
H19B0.84700.22680.48420.073*
H19C0.78330.29930.39380.073*
C201.0318 (4)0.2944 (4)0.6096 (4)0.0551 (14)
H20A0.97030.30430.63840.083*
H20B1.08660.32930.65660.083*
H20C1.04570.21700.60480.083*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0354 (3)0.0546 (4)0.0368 (4)−0.0007 (3)0.0008 (3)0.0014 (3)
N10.0296 (19)0.045 (2)0.029 (2)0.0054 (17)0.0013 (15)−0.0004 (17)
N20.034 (2)0.052 (3)0.035 (2)0.0108 (19)−0.0008 (17)−0.0133 (18)
N30.0277 (19)0.043 (2)0.029 (2)−0.0016 (16)0.0040 (15)0.0005 (16)
N40.0308 (19)0.042 (2)0.030 (2)−0.0009 (16)0.0009 (16)−0.0070 (16)
O10.0438 (19)0.053 (2)0.0376 (19)0.0011 (15)−0.0052 (15)0.0100 (15)
O20.051 (2)0.105 (3)0.044 (2)0.028 (2)−0.0141 (18)−0.015 (2)
O30.0358 (18)0.067 (2)0.0329 (18)−0.0040 (16)−0.0014 (14)0.0100 (16)
O40.042 (2)0.075 (3)0.038 (2)0.0039 (17)−0.0102 (16)−0.0068 (16)
O50.048 (2)0.098 (3)0.048 (2)0.028 (2)−0.0204 (16)−0.032 (2)
C10.042 (3)0.046 (3)0.035 (3)0.012 (2)0.011 (2)0.007 (2)
C20.052 (3)0.057 (3)0.034 (3)0.024 (3)0.009 (2)0.005 (2)
C30.037 (3)0.072 (4)0.032 (3)0.025 (3)−0.004 (2)−0.010 (3)
C40.028 (2)0.043 (3)0.029 (2)0.004 (2)0.0021 (19)−0.006 (2)
C50.034 (3)0.039 (3)0.040 (3)0.003 (2)0.008 (2)−0.002 (2)
C60.049 (3)0.042 (3)0.062 (4)0.002 (2)0.014 (3)0.003 (2)
C70.049 (3)0.043 (3)0.092 (5)−0.005 (3)0.005 (3)−0.017 (3)
C80.037 (3)0.066 (4)0.068 (4)−0.004 (3)−0.006 (3)−0.031 (3)
C90.062 (3)0.052 (3)0.062 (4)0.005 (3)0.013 (3)0.017 (3)
C100.071 (4)0.078 (4)0.046 (3)0.034 (3)0.006 (3)0.018 (3)
C110.040 (3)0.038 (3)0.028 (3)0.003 (2)0.008 (2)0.002 (2)
C120.047 (3)0.035 (3)0.026 (2)0.004 (2)0.002 (2)−0.0003 (19)
C130.041 (3)0.038 (3)0.030 (3)0.006 (2)−0.004 (2)−0.008 (2)
C140.029 (2)0.037 (2)0.027 (2)0.0029 (19)0.0013 (18)−0.0050 (18)
C150.037 (3)0.042 (3)0.028 (3)−0.001 (2)0.004 (2)−0.004 (2)
C160.050 (3)0.060 (3)0.031 (3)−0.011 (2)0.010 (2)0.000 (2)
C170.047 (3)0.067 (4)0.046 (3)−0.014 (3)0.015 (3)−0.007 (3)
C180.029 (3)0.067 (3)0.047 (3)−0.010 (2)0.005 (2)−0.008 (3)
C190.046 (3)0.061 (3)0.040 (3)−0.004 (2)0.012 (2)0.004 (2)
C200.064 (3)0.060 (3)0.037 (3)0.002 (3)−0.004 (3)0.007 (2)

Geometric parameters (Å, °)

Ni1—O31.959 (3)C6—H60.9300
Ni1—O11.964 (3)C7—C81.338 (8)
Ni1—O51.991 (3)C7—H70.9300
Ni1—N32.155 (3)C8—H80.9300
Ni1—N12.160 (3)C9—H9A0.9600
N1—C41.329 (5)C9—H9B0.9600
N1—C11.360 (5)C9—H9C0.9600
N2—C41.370 (5)C10—H10A0.9600
N2—C81.387 (6)C10—H10B0.9600
N2—C31.429 (6)C10—H10C0.9600
N3—C141.327 (5)C11—C121.374 (6)
N3—C111.361 (5)C11—C191.503 (6)
N4—C141.368 (5)C12—C131.406 (6)
N4—C181.389 (5)C12—C201.505 (6)
N4—C131.433 (6)C14—C151.445 (6)
O1—C51.297 (5)C15—C161.374 (6)
O2—C31.239 (5)C16—C171.390 (7)
O3—C151.301 (5)C16—H160.9300
O4—C131.241 (5)C17—C181.347 (7)
O5—H5A0.8499C17—H170.9300
O5—H5B0.8499C18—H180.9300
C1—C21.379 (6)C19—H19A0.9600
C1—C91.491 (7)C19—H19B0.9600
C2—C31.401 (7)C19—H19C0.9600
C2—C101.511 (7)C20—H20A0.9600
C4—C51.442 (6)C20—H20B0.9600
C5—C61.370 (6)C20—H20C0.9600
C6—C71.395 (7)
O3—Ni1—O1132.53 (14)N2—C8—H8119.8
O3—Ni1—O5115.52 (16)C1—C9—H9A109.5
O1—Ni1—O5111.75 (15)C1—C9—H9B109.5
O3—Ni1—N380.38 (12)H9A—C9—H9B109.5
O1—Ni1—N3100.05 (13)C1—C9—H9C109.5
O5—Ni1—N394.82 (13)H9A—C9—H9C109.5
O3—Ni1—N193.07 (13)H9B—C9—H9C109.5
O1—Ni1—N180.18 (13)C2—C10—H10A109.5
O5—Ni1—N193.07 (13)C2—C10—H10B109.5
N3—Ni1—N1171.37 (13)H10A—C10—H10B109.5
C4—N1—C1119.3 (4)C2—C10—H10C109.5
C4—N1—Ni1108.5 (3)H10A—C10—H10C109.5
C1—N1—Ni1132.2 (3)H10B—C10—H10C109.5
C4—N2—C8120.3 (4)N3—C11—C12122.3 (4)
C4—N2—C3120.1 (4)N3—C11—C19115.5 (4)
C8—N2—C3119.6 (4)C12—C11—C19122.2 (4)
C14—N3—C11118.7 (3)C11—C12—C13120.4 (4)
C14—N3—Ni1108.2 (3)C11—C12—C20122.8 (4)
C11—N3—Ni1133.0 (3)C13—C12—C20116.8 (4)
C14—N4—C18120.9 (4)O4—C13—C12127.5 (4)
C14—N4—C13120.4 (4)O4—C13—N4117.0 (4)
C18—N4—C13118.7 (4)C12—C13—N4115.5 (4)
C5—O1—Ni1116.0 (3)N3—C14—N4122.7 (4)
C15—O3—Ni1115.7 (3)N3—C14—C15117.7 (4)
Ni1—O5—H5A120.6N4—C14—C15119.6 (4)
Ni1—O5—H5B129.2O3—C15—C16124.7 (4)
H5A—O5—H5B110.1O3—C15—C14117.3 (4)
N1—C1—C2121.4 (4)C16—C15—C14118.0 (4)
N1—C1—C9115.8 (4)C15—C16—C17119.9 (4)
C2—C1—C9122.8 (4)C15—C16—H16120.0
C1—C2—C3120.8 (4)C17—C16—H16120.0
C1—C2—C10122.5 (5)C18—C17—C16122.4 (5)
C3—C2—C10116.7 (5)C18—C17—H17118.8
O2—C3—C2127.7 (5)C16—C17—H17118.8
O2—C3—N2116.4 (5)C17—C18—N4119.1 (4)
C2—C3—N2115.9 (4)C17—C18—H18120.4
N1—C4—N2122.6 (4)N4—C18—H18120.4
N1—C4—C5117.4 (4)C11—C19—H19A109.5
N2—C4—C5120.0 (4)C11—C19—H19B109.5
O1—C5—C6124.8 (4)H19A—C19—H19B109.5
O1—C5—C4117.8 (4)C11—C19—H19C109.5
C6—C5—C4117.4 (4)H19A—C19—H19C109.5
C5—C6—C7121.0 (5)H19B—C19—H19C109.5
C5—C6—H6119.5C12—C20—H20A109.5
C7—C6—H6119.5C12—C20—H20B109.5
C8—C7—C6121.0 (5)H20A—C20—H20B109.5
C8—C7—H7119.5C12—C20—H20C109.5
C6—C7—H7119.5H20A—C20—H20C109.5
C7—C8—N2120.3 (5)H20B—C20—H20C109.5
C7—C8—H8119.8
O3—Ni1—N1—C4133.7 (3)N1—C4—C5—O1−2.3 (6)
O1—Ni1—N1—C41.0 (3)N2—C4—C5—O1178.5 (4)
O5—Ni1—N1—C4−110.5 (3)N1—C4—C5—C6177.6 (4)
O3—Ni1—N1—C1−44.8 (4)N2—C4—C5—C6−1.6 (6)
O1—Ni1—N1—C1−177.5 (4)O1—C5—C6—C7179.7 (4)
O5—Ni1—N1—C171.0 (4)C4—C5—C6—C7−0.1 (7)
O3—Ni1—N3—C146.0 (3)C5—C6—C7—C81.1 (8)
O1—Ni1—N3—C14137.8 (3)C6—C7—C8—N2−0.4 (8)
O5—Ni1—N3—C14−109.1 (3)C4—N2—C8—C7−1.4 (7)
O3—Ni1—N3—C11−176.6 (4)C3—N2—C8—C7−179.5 (5)
O1—Ni1—N3—C11−44.9 (4)C14—N3—C11—C121.0 (6)
O5—Ni1—N3—C1168.3 (4)Ni1—N3—C11—C12−176.2 (3)
O3—Ni1—O1—C5−87.5 (3)C14—N3—C11—C19−179.6 (4)
O5—Ni1—O1—C587.0 (3)Ni1—N3—C11—C193.3 (6)
N3—Ni1—O1—C5−173.6 (3)N3—C11—C12—C130.2 (7)
N1—Ni1—O1—C5−2.4 (3)C19—C11—C12—C13−179.2 (4)
O1—Ni1—O3—C15−102.8 (3)N3—C11—C12—C20−179.0 (4)
O5—Ni1—O3—C1582.8 (3)C19—C11—C12—C201.7 (7)
N3—Ni1—O3—C15−8.0 (3)C11—C12—C13—O4179.3 (4)
N1—Ni1—O3—C15177.7 (3)C20—C12—C13—O4−1.6 (7)
C4—N1—C1—C20.9 (6)C11—C12—C13—N4−0.3 (6)
Ni1—N1—C1—C2179.3 (3)C20—C12—C13—N4178.9 (4)
C4—N1—C1—C9179.9 (4)C14—N4—C13—O4179.8 (4)
Ni1—N1—C1—C9−1.7 (6)C18—N4—C13—O4−1.2 (6)
N1—C1—C2—C30.5 (7)C14—N4—C13—C12−0.6 (6)
C9—C1—C2—C3−178.4 (4)C18—N4—C13—C12178.4 (4)
N1—C1—C2—C10−178.7 (4)C11—N3—C14—N4−2.0 (6)
C9—C1—C2—C102.4 (7)Ni1—N3—C14—N4175.8 (3)
C1—C2—C3—O2179.4 (4)C11—N3—C14—C15178.7 (4)
C10—C2—C3—O2−1.4 (7)Ni1—N3—C14—C15−3.5 (4)
C1—C2—C3—N2−0.9 (6)C18—N4—C14—N3−177.2 (4)
C10—C2—C3—N2178.3 (4)C13—N4—C14—N31.8 (6)
C4—N2—C3—O2179.7 (4)C18—N4—C14—C152.2 (6)
C8—N2—C3—O2−2.1 (6)C13—N4—C14—C15−178.8 (4)
C4—N2—C3—C20.0 (6)Ni1—O3—C15—C16−171.8 (4)
C8—N2—C3—C2178.2 (4)Ni1—O3—C15—C148.5 (5)
C1—N1—C4—N2−1.9 (6)N3—C14—C15—O3−2.9 (6)
Ni1—N1—C4—N2179.4 (3)N4—C14—C15—O3177.8 (4)
C1—N1—C4—C5179.0 (4)N3—C14—C15—C16177.5 (4)
Ni1—N1—C4—C50.3 (4)N4—C14—C15—C16−1.9 (6)
C8—N2—C4—N1−176.8 (4)O3—C15—C16—C17−179.2 (4)
C3—N2—C4—N11.4 (6)C14—C15—C16—C170.4 (7)
C8—N2—C4—C52.3 (6)C15—C16—C17—C180.8 (8)
C3—N2—C4—C5−179.5 (4)C16—C17—C18—N4−0.6 (8)
Ni1—O1—C5—C6−176.6 (3)C14—N4—C18—C17−0.9 (7)
Ni1—O1—C5—C43.3 (5)C13—N4—C18—C17−179.9 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5A···O2i0.851.832.672 (5)173
O5—H5B···O4ii0.851.852.669 (5)162

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2018).

References

  • Bayot, D., Degand, M., Tinant, B. & Devillers, M. (2006). Inorg. Chem. Commun.359, 1390–1394.
  • Chen, K., Zhang, Y.-L., Feng, M.-Q. & Liu, C.-H. (2007). Acta Cryst. E63, m2033.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sun, Y., Jiang, X.-D. & Li, X.-B. (2008). Acta Cryst. E64, m801. [PMC free article] [PubMed]
  • Wei, Y.-F., Li, Z.-S., Zhang, H.-H. & Wang, Y.-H. (2009). Acta Cryst. E65, m91. [PMC free article] [PubMed]
  • Wu, H., Dong, X.-W., Liu, H.-Y. & Ma, J.-F. (2006). Acta Cryst. E62, m281–m282.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography