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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1977
https://doi.org/10.1107/S1600536810026206

N-(4-Chloro­phen­yl)-2-(8-quinol­yl­oxy)acetamide monohydrate

Yuan Wang,a* Yan-Wei Lia and Xiao-Xia Lib

aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China, and bInstitute of Functional Materials, Jiangxi University of Finance & Economics, Nanchang 330013, People's Republic of China
*Correspondence e-mail: wangyuan08@hpu.edu.cn

(Received 29 June 2010; accepted 3 July 2010; online 10 July 2010)

In the title compound, C17H13ClN2O2·H2O, the dihedral angle between the quinoline ring system and the benzene ring is 13.0 (1)°. An intra­molecular N—H⋯O hydrogen bond may influence the mol­ecular conformation. In the crystal structure, acetamide mol­ecules are linked to water mol­ecules via inter­molecular O—H⋯ N and N—H⋯O hydrogen bonds and in turn linked into chains along [010] via O—H⋯O hydrogen bonds.

Related literature

For the synthesis of the title compound and its lanthanide complexes, see: Wu et al. (2008[Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.]). For related structures, see: Zhang et al. (2006[Zhang, S.-S., Xu, L.-L., Wen, H.-L., Li, X.-M. & Wen, Y.-H. (2006). Acta Cryst. E62, o3071-o3072.]); Wu et al. (2010[Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.]).

[Scheme 1]

Experimental

Crystal data

  • C17H13ClN2O2·H2O

  • Mr = 330.76

  • Orthorhombic, P b c a

  • a = 19.4984 (19) Å

  • b = 5.2601 (6) Å

  • c = 29.851 (3) Å

  • V = 3061.7 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 296 K

  • 0.32 × 0.23 × 0.20 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.929, Tmax = 0.948

  • 15222 measured reflections

  • 3622 independent reflections

  • 1800 reflections with I > 2σ(I)

  • Rint = 0.050
Refinement

  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.128

  • S = 1.00

  • 3622 reflections

  • 217 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1W—H1WA⋯O1Wi 0.85 (1) 2.06 (1) 2.9014 (16) 168 (2)
O1W—H1WB⋯N2 0.85 (1) 1.99 (1) 2.830 (2) 170 (2)
N1—H1A⋯O2 0.83 (1) 2.27 (2) 2.702 (2) 113 (2)
N1—H1A⋯O1W 0.83 (1) 2.40 (2) 3.088 (2) 140 (2)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810026206/lh5076sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026206/lh5076Isup2.hkl

checkCIF report


Comment top

Amide type ligands have been extensively investigated due to their excellent coordination abilities (Wu et al., 2008;2010). As part of our ongoing studies of amide type ligands, the title compound was synthesized and characterized by X-ray diffraction.

In the title compound, all the bond lengths are comparable with those observed in a similar compound (Zhang et al., 2006). The dihedral angle between quinoline ring (N2/C9–C17, r.m.s. deviation 0.0129 Å) and benzene ring (C1–C6, r.m.s. deviation 0.0008 Å) is 13.0 (1)°. An intramolecular N-H···O hydrogen bond may influence the molecular conformation. In the crystal structure, N-(4-chlorophenyl)-2- (quinolin-8-yloxy)acetamide molecules are linked to water molecules via intermolecular O—H··· N and N—H···O hydrogen bonds and in turn linked into one-dimensional chains along [010] via O-H···O hydrogen bonds. Additional stabilization is provided by weak π···π stacking interactions involving the benzene ring and pyridine rings of symmetry related quinoline groups with a centroid to centroid distance of 3.8607 (14) Å.

Related literature top

For the synthesis of the title compound and its lanthanide complexes, see: Wu et al. (2008). For related structures, see: Zhang et al. (2006); Wu et al. (2010).

Experimental top

The title compound was prepared according to the literature, Wu et al. (2008). Colorless block crystals were obtained by slow evaporation of a N,N-dimethylformamide solution of the title compound.

Refinement top

The N—H and water H-atoms were located in a difference Fourier map and refined with an N—H distance restraint of 0.83 (1)Å and an O—H distance restraint of 0.85 (1)Å. H atoms attached to C atoms were placed in calculated positions and treated using a riding-model approximation (C—H = 0.93; Uiso(H)=1.2Ueq(C)).

Structure description top

Amide type ligands have been extensively investigated due to their excellent coordination abilities (Wu et al., 2008;2010). As part of our ongoing studies of amide type ligands, the title compound was synthesized and characterized by X-ray diffraction.

In the title compound, all the bond lengths are comparable with those observed in a similar compound (Zhang et al., 2006). The dihedral angle between quinoline ring (N2/C9–C17, r.m.s. deviation 0.0129 Å) and benzene ring (C1–C6, r.m.s. deviation 0.0008 Å) is 13.0 (1)°. An intramolecular N-H···O hydrogen bond may influence the molecular conformation. In the crystal structure, N-(4-chlorophenyl)-2- (quinolin-8-yloxy)acetamide molecules are linked to water molecules via intermolecular O—H··· N and N—H···O hydrogen bonds and in turn linked into one-dimensional chains along [010] via O-H···O hydrogen bonds. Additional stabilization is provided by weak π···π stacking interactions involving the benzene ring and pyridine rings of symmetry related quinoline groups with a centroid to centroid distance of 3.8607 (14) Å.

For the synthesis of the title compound and its lanthanide complexes, see: Wu et al. (2008). For related structures, see: Zhang et al. (2006); Wu et al. (2010).

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
[Figure 1] Fig. 1. The molecular structure shown with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure viewed approximately along the b axis with hydrogen bonds shown as dashed lines.
N-(4-Chlorophenyl)-2-(8-quinolyloxy)acetamide monohydrate top
Crystal data top
C17H13ClN2O2·H2OF(000) = 1376
Mr = 330.76Dx = 1.435 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1957 reflections
a = 19.4984 (19) Åθ = 2.5–19.9°
b = 5.2601 (6) ŵ = 0.27 mm−1
c = 29.851 (3) ÅT = 296 K
V = 3061.7 (5) Å3Block, colorless
Z = 80.32 × 0.23 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer		3622 independent reflections
Radiation source: sealed tube1800 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 28.1°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −18→25
Tmin = 0.929, Tmax = 0.948k = −6→4
15222 measured reflectionsl = −39→39
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0231P]
where P = (Fo2 + 2Fc2)/3
3622 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.16 e Å−3
4 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C17H13ClN2O2·H2OV = 3061.7 (5) Å3
Mr = 330.76Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 19.4984 (19) ŵ = 0.27 mm−1
b = 5.2601 (6) ÅT = 296 K
c = 29.851 (3) Å0.32 × 0.23 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer		3622 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1800 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 0.948Rint = 0.050
15222 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0474 restraints
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.16 e Å−3
3622 reflectionsΔρmin = −0.21 e Å−3
217 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
xyzUiso*/Ueq
Cl10.32260 (4)0.36909 (15)0.044180 (19)0.0858 (3)
O20.40858 (7)0.1726 (3)0.32297 (4)0.0532 (4)
N20.34502 (9)0.5390 (3)0.36817 (6)0.0505 (5)
N10.38877 (10)0.1567 (3)0.23341 (6)0.0524 (5)
C100.47572 (12)0.0589 (4)0.38814 (7)0.0568 (6)
H100.4991−0.06750.37260.068*
C170.39211 (11)0.3959 (4)0.39023 (6)0.0454 (5)
C130.40699 (12)0.4337 (4)0.43606 (7)0.0522 (6)
C70.42016 (11)−0.0454 (4)0.25142 (7)0.0506 (6)
C90.42715 (11)0.2012 (4)0.36669 (6)0.0470 (5)
C110.49027 (12)0.1029 (5)0.43328 (8)0.0647 (7)
H110.52380.00600.44740.078*
C120.45676 (13)0.2827 (4)0.45688 (7)0.0618 (7)
H120.46670.30650.48710.074*
C140.37041 (14)0.6238 (5)0.45851 (7)0.0650 (7)
H140.37820.65220.48880.078*
O10.43645 (9)−0.2349 (3)0.23095 (5)0.0771 (5)
C10.34138 (12)0.3011 (5)0.09954 (7)0.0564 (6)
C80.43823 (12)−0.0380 (4)0.30005 (7)0.0529 (6)
H8A0.4228−0.19420.31410.063*
H8B0.4877−0.02980.30300.063*
C40.37288 (11)0.1944 (4)0.18780 (7)0.0480 (5)
C30.33244 (12)0.3998 (4)0.17682 (7)0.0569 (6)
H30.31550.50390.19950.068*
C20.31662 (12)0.4537 (5)0.13280 (7)0.0612 (6)
H20.28930.59300.12580.073*
C160.31355 (12)0.7171 (5)0.39060 (7)0.0619 (6)
H160.28220.81810.37530.074*
C60.38144 (13)0.0964 (5)0.10979 (7)0.0649 (7)
H60.3982−0.00700.08700.078*
C50.39718 (13)0.0424 (4)0.15377 (7)0.0629 (7)
H50.4244−0.09770.16050.075*
C150.32395 (14)0.7662 (5)0.43632 (8)0.0681 (7)
H150.29950.89340.45090.082*
O1W0.28141 (9)0.4811 (3)0.28357 (5)0.0696 (5)
H1A0.3792 (14)0.272 (4)0.2514 (7)0.104*
H1WA0.2599 (13)0.621 (3)0.2800 (7)0.104*
H1WB0.3043 (12)0.488 (5)0.3078 (6)0.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0970 (6)0.1067 (6)0.0538 (4)−0.0048 (5)−0.0072 (3)0.0087 (4)
O20.0583 (10)0.0571 (10)0.0443 (8)0.0109 (8)−0.0004 (7)−0.0023 (7)
N20.0479 (11)0.0527 (11)0.0509 (10)0.0024 (10)0.0006 (9)−0.0023 (9)
N10.0637 (13)0.0479 (12)0.0455 (11)0.0084 (10)0.0035 (9)−0.0050 (9)
C100.0559 (15)0.0596 (15)0.0548 (13)0.0078 (13)0.0008 (11)0.0075 (11)
C170.0428 (13)0.0474 (13)0.0460 (12)−0.0093 (11)0.0013 (10)0.0031 (10)
C130.0564 (16)0.0522 (14)0.0479 (13)−0.0131 (12)0.0007 (11)0.0020 (11)
C70.0553 (15)0.0433 (13)0.0533 (13)−0.0019 (12)0.0051 (11)−0.0029 (11)
C90.0467 (13)0.0514 (14)0.0431 (11)−0.0045 (11)0.0017 (10)0.0048 (10)
C110.0607 (17)0.0717 (17)0.0618 (15)0.0002 (14)−0.0119 (13)0.0128 (13)
C120.0712 (18)0.0652 (17)0.0490 (13)−0.0091 (14)−0.0092 (13)0.0060 (12)
C140.080 (2)0.0656 (17)0.0492 (14)−0.0122 (15)0.0029 (13)−0.0056 (12)
O10.1077 (15)0.0544 (11)0.0691 (10)0.0222 (10)−0.0111 (10)−0.0142 (9)
C10.0581 (16)0.0621 (16)0.0490 (13)−0.0105 (13)0.0011 (11)0.0007 (12)
C80.0611 (16)0.0450 (13)0.0525 (13)0.0043 (12)0.0072 (11)0.0048 (11)
C40.0503 (15)0.0452 (12)0.0485 (12)−0.0055 (11)0.0031 (11)−0.0035 (10)
C30.0629 (16)0.0520 (14)0.0558 (14)0.0068 (13)−0.0027 (12)−0.0110 (11)
C20.0615 (15)0.0600 (15)0.0621 (15)0.0043 (13)−0.0094 (13)−0.0010 (12)
C160.0584 (16)0.0599 (15)0.0673 (15)0.0036 (13)−0.0009 (13)−0.0050 (13)
C60.0829 (19)0.0631 (16)0.0486 (14)0.0028 (15)0.0136 (13)−0.0053 (12)
C50.0821 (18)0.0527 (14)0.0539 (14)0.0125 (13)0.0141 (13)−0.0024 (11)
C150.0737 (19)0.0673 (17)0.0634 (16)−0.0007 (15)0.0090 (14)−0.0175 (14)
O1W0.0808 (14)0.0720 (13)0.0560 (10)0.0091 (10)−0.0059 (9)−0.0056 (9)
Geometric parameters (Å, º) top
Cl1—C11.730 (2)C14—C151.349 (3)
O2—C91.363 (2)C14—H140.9300
O2—C81.425 (2)C1—C61.365 (3)
N2—C161.305 (3)C1—C21.365 (3)
N2—C171.358 (2)C8—H8A0.9700
N1—C71.339 (3)C8—H8B0.9700
N1—C41.411 (3)C4—C51.377 (3)
N1—H1A0.832 (10)C4—C31.377 (3)
C10—C91.366 (3)C3—C21.379 (3)
C10—C111.396 (3)C3—H30.9300
C10—H100.9300C2—H20.9300
C17—C131.412 (3)C16—C151.404 (3)
C17—C91.417 (3)C16—H160.9300
C13—C121.400 (3)C6—C51.378 (3)
C13—C141.399 (3)C6—H60.9300
C7—O11.212 (2)C5—H50.9300
C7—C81.494 (3)C15—H150.9300
C11—C121.348 (3)O1W—H1WA0.854 (9)
C11—H110.9300O1W—H1WB0.851 (9)
C12—H120.9300
C9—O2—C8115.98 (16)C6—C1—Cl1119.91 (18)
C16—N2—C17117.87 (19)C2—C1—Cl1119.9 (2)
C7—N1—C4126.84 (18)O2—C8—C7113.02 (17)
C7—N1—H1A115.0 (19)O2—C8—H8A109.0
C4—N1—H1A118.2 (19)C7—C8—H8A109.0
C9—C10—C11120.1 (2)O2—C8—H8B109.0
C9—C10—H10119.9C7—C8—H8B109.0
C11—C10—H10119.9H8A—C8—H8B107.8
N2—C17—C13122.04 (19)C5—C4—C3118.5 (2)
N2—C17—C9119.08 (18)C5—C4—N1123.7 (2)
C13—C17—C9118.88 (19)C3—C4—N1117.76 (19)
C12—C13—C14123.1 (2)C4—C3—C2121.1 (2)
C12—C13—C17119.5 (2)C4—C3—H3119.5
C14—C13—C17117.4 (2)C2—C3—H3119.5
O1—C7—N1124.8 (2)C1—C2—C3119.6 (2)
O1—C7—C8116.7 (2)C1—C2—H2120.2
N1—C7—C8118.50 (19)C3—C2—H2120.2
O2—C9—C10124.9 (2)N2—C16—C15124.3 (2)
O2—C9—C17115.25 (18)N2—C16—H16117.9
C10—C9—C17119.84 (19)C15—C16—H16117.9
C12—C11—C10121.5 (2)C1—C6—C5120.3 (2)
C12—C11—H11119.3C1—C6—H6119.9
C10—C11—H11119.3C5—C6—H6119.9
C11—C12—C13120.1 (2)C4—C5—C6120.4 (2)
C11—C12—H12119.9C4—C5—H5119.8
C13—C12—H12119.9C6—C5—H5119.8
C15—C14—C13120.3 (2)C14—C15—C16118.2 (2)
C15—C14—H14119.9C14—C15—H15120.9
C13—C14—H14119.9C16—C15—H15120.9
C6—C1—C2120.2 (2)H1WA—O1W—H1WB109.2 (15)
C16—N2—C17—C130.5 (3)C12—C13—C14—C15178.8 (2)
C16—N2—C17—C9−179.92 (19)C17—C13—C14—C15−1.2 (3)
N2—C17—C13—C12−179.1 (2)C9—O2—C8—C7−175.30 (17)
C9—C17—C13—C121.3 (3)O1—C7—C8—O2−171.25 (19)
N2—C17—C13—C140.9 (3)N1—C7—C8—O210.0 (3)
C9—C17—C13—C14−178.67 (19)C7—N1—C4—C5−10.4 (4)
C4—N1—C7—O1−4.3 (4)C7—N1—C4—C3171.6 (2)
C4—N1—C7—C8174.31 (19)C5—C4—C3—C2−0.2 (3)
C8—O2—C9—C106.1 (3)N1—C4—C3—C2177.9 (2)
C8—O2—C9—C17−174.00 (17)C6—C1—C2—C30.1 (3)
C11—C10—C9—O2−179.4 (2)Cl1—C1—C2—C3−179.29 (18)
C11—C10—C9—C170.8 (3)C4—C3—C2—C10.0 (3)
N2—C17—C9—O2−1.3 (3)C17—N2—C16—C15−1.7 (3)
C13—C17—C9—O2178.33 (18)C2—C1—C6—C50.0 (4)
N2—C17—C9—C10178.64 (19)Cl1—C1—C6—C5179.38 (19)
C13—C17—C9—C10−1.8 (3)C3—C4—C5—C60.3 (3)
C9—C10—C11—C120.7 (4)N1—C4—C5—C6−177.6 (2)
C10—C11—C12—C13−1.2 (4)C1—C6—C5—C4−0.2 (4)
C14—C13—C12—C11−179.9 (2)C13—C14—C15—C160.2 (4)
C17—C13—C12—C110.1 (3)N2—C16—C15—C141.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O1Wi0.85 (1)2.06 (1)2.9014 (16)168 (2)
N1—H1A···O20.83 (1)2.27 (2)2.702 (2)113 (2)
N1—H1A···O1W0.83 (1)2.40 (2)3.088 (2)140 (2)
O1W—H1WB···N20.85 (1)1.99 (1)2.830 (2)170 (2)
Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC17H13ClN2O2·H2O
Mr330.76
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)19.4984 (19), 5.2601 (6), 29.851 (3)
V (Å3)3061.7 (5)
Z8
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.32 × 0.23 × 0.20
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.929, 0.948
No. of measured, independent and
observed [I > 2σ(I)] reflections		15222, 3622, 1800
Rint0.050
(sin θ/λ)max (Å−1)0.663
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.128, 1.00
No. of reflections3622
No. of parameters217
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.16, −0.21

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···AD—HH···AD···AD—H···A
O1W—H1WA···O1Wi0.854 (9)2.061 (12)2.9014 (16)168 (2)
N1—H1A···O20.832 (10)2.27 (2)2.702 (2)113 (2)
N1—H1A···O1W0.832 (10)2.401 (19)3.088 (2)140 (2)
O1W—H1WB···N20.851 (9)1.988 (11)2.830 (2)170 (2)
Symmetry code: (i) −x+1/2, y+1/2, z.
 

Acknowledgements

The authors are grateful for financial support from the Doctoral Foundation of Henan Polytechnic University (B2009–70 648359).

References

First citationBruker (1997). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207–2215.  Web of Science CrossRef CAS Google Scholar
 First citationWu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationZhang, S.-S., Xu, L.-L., Wen, H.-L., Li, X.-M. & Wen, Y.-H. (2006). Acta Cryst. E62, o3071–o3072.  Web of Science CSD CrossRef 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.

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1977
https://doi.org/10.1107/S1600536810026206
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