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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1111–o1112.
Published online 2010 April 17. doi:  10.1107/S1600536810013644
PMCID: PMC2979020

2-(4-Methoxy­phen­yl)-6-trifluoro­methyl-1H-pyrrolo[3,2-c]quinoline monohydrate

Abstract

In the title compound, C19H13F3N2O·H2O, the phenyl and pyrroloquinoline ring system are close to coplanar [dihedral angle = 10.94 (4)°]. The meth­oxy group also is almost coplanar with the phenyl ring [5.4 (1)°]. In the crystal structure N—H(...)O(water) and water–quinoline O—H(...)N hydrogen bonds build up a supra­molecular chain-like arrangement along [001]. The remaining H atom of the water mol­ecule does not take part in classical hydrogen bonds. Instead, this O—H bond points toward the center of the phenyl ring of a neighbouring mol­ecule. Weak C—H(...)O and C—H(...)π inter­actions are also present.

Related literature

For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]). For O—H(...)π bonds, see: Atwood et al. (1991 [triangle]). For the graph-set description of hydrogen-bond systems, see: Bernstein et al. (1995 [triangle]). For the influence of substituents on the geometry of aromatic rings, see: Domenicano (1988 [triangle]). For a similar synthesis, see: Dutkiewicz et al. (2010 [triangle]). For related structures, see: Fan & Chen (1987 [triangle]); Lynch et al. (2001 [triangle]); Lynch & McClenaghan (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1111-scheme1.jpg

Experimental

Crystal data

  • C19H13F3N2O·H2O
  • M r = 360.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1111-efi1.jpg
  • a = 13.838 (1) Å
  • b = 7.0432 (5) Å
  • c = 17.758 (2) Å
  • β = 102.743 (8)°
  • V = 1688.2 (2) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.99 mm−1
  • T = 295 K
  • 0.4 × 0.2 × 0.1 mm

Data collection

  • Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 [triangle]) T min = 0.340, T max = 1.000
  • 5601 measured reflections
  • 3304 independent reflections
  • 2767 reflections with I > 2σ(I)
  • R int = 0.013

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.128
  • S = 1.07
  • 3304 reflections
  • 296 parameters
  • All H-atom parameters refined
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 [triangle]) and Mercury (Macrae et al., 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013644/im2190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013644/im2190Isup2.hkl

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

Acknowledgments

ANM thanks the University of Mysore for the research facilities.

supplementary crystallographic information

Comment

There is only one crystal structure of a compound having a pyrrolo[3,2-c]quinoline skeleton in the Cambridge Crystallographic Database (Allen, 2002; Version 5.31 of November 2009, last update Feb. 2010): 1-phenyl-2,3,4-tris(trifluoromethyl)pyrrolo[2,3-c]quinoline (Fan & Chen, 1987). The only other similar structurally characterized compounds are derivatives of 1H-pyrrolo[2,3-h]quinoline, namely 2-(4-pyridyl)-pyrrolo[3,2-h]quinoline (Lynch et al., 2001) and 2-phenylpyrrolo[2,3-h]quinoline dihydrate (Lynch & McClenaghan, 2002). Here we present the results of the crystal structure determination of 2-(4-methoxyphenyl)-6-(trifluoromethyl)-1H-pyrrolo[3,2-c]quinoline hydrate(1 . H2O, Scheme 1).

Two planar systems in (1), pyrroloquinoline (planar within 0.0171 (4) Å) and the phenyl ring (0.0050 (11) Å) make a dihedral angle of 10.94 (4)°. Therefore, the complete molecule (without F atoms) is approximately planar. The methoxy group also is not twisted significantly (5.4 (1)°) with respect to the phenyl ring plane. Bond angles within the phenyl ring are influenced by the presence of substituents. As expected for p-disubstitution, the influences are almost additive. The sum of values given by Domenicano (1988) or found in the CSD for mono-substituted phenyl rings are very close to the actual values in (1).

The primary motif of the crystal packing is a chain of alternate water and 1 molecules (Fig. 2, Table 1). In that chain (C22(8) using graph set notation: Bernstein et al., 1995) both components act as hydrogen bond donor and acceptor. N11—H11 group of 1 donates hydrogen for the N—H···O1W (water) hydrogen bond, and the water molecule acts as a donor for the OH···N1(quinoline) hydrogen bond. Due to the steric requirement, the O1W oxygen atom is also in close contact with the adjacent H6 and H19 hydrogen atoms. Because of the geometric parameters of these interactions (Table 1), they might be regarded as the secondary, weak hydrogen bonds. The remaining hydrogen atom of the water molecule does not take part in "classical" hydrogen bonds; instead this O—H bond points toward the phenyl ring of the neighbouring molecule, probably making the O—H(water)···π weak hydrogen bond. Such hydrogen bonds were described by Atwood et al. (1991), and they are supposed to play a role in the biological systems. There are some 300 cases of such short contacts in the CSD. In 1, O—H···π hydrogen bonds together with another weak interactions of C—H···O, C—H···π and π···π type, connect the neighbouring chains (Table 1, Fig. 3).

Experimental

1-(4-methoxyphenyl)ethanone [8-(trifluoromethyl)quinolin-4-yl]hydrazone (1.8 g, 5 mmoles), prepared according to the previously described method (Dutkiewicz et al., 2010) was added to 5 ml of diphenyl ether and the mixture was heated at 523 K in an oil bath for 6 hrs. After cooling, ether was added until the solution became cloudy. Further cooling resulted in precipitation of the product (I), which was collected by filtration. Recrystallization was performed at room temperature from ethanol, m.p.: 401-403 K. Analysis found: C 66.56, H 3.79, N 8.23%; C19H13F3N2O, requires: C 66.66, H 3.83, N 8.18%

Refinement

Hydrogen atoms were located in the difference Fourier maps and isotropically refined.

Figures

Fig. 1.
Anisotropic ellipsoid representation of the compound 1 . H2O showing the atom labelling scheme. Ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii. Hydrogen bonds and weaker C—H···O ...
Fig. 2.
Hydrogen bonded chain along [001]; N—H···O, O—H···N, and C—H···O hydrogen bonds are shown as dashed lines.
Fig. 3.
The crystal packing; hydrogen bonds and O—H···π and C—H···π contacts are shown as dashed lines.

Crystal data

C19H13F3N2O·H2OF(000) = 744
Mr = 360.33Dx = 1.418 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 3587 reflections
a = 13.838 (1) Åθ = 3.3–75.2°
b = 7.0432 (5) ŵ = 0.99 mm1
c = 17.758 (2) ÅT = 295 K
β = 102.743 (8)°Plate, colourless
V = 1688.2 (2) Å30.4 × 0.2 × 0.1 mm
Z = 4

Data collection

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer3304 independent reflections
Radiation source: SuperNova (Cu) X-ray Source2767 reflections with I > 2σ(I)
mirrorRint = 0.013
Detector resolution: 5.2679 pixels mm-1θmax = 75.3°, θmin = 3.3°
ω scansh = −17→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −8→5
Tmin = 0.340, Tmax = 1.000l = −22→19
5601 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041All H-atom parameters refined
wR(F2) = 0.128w = 1/[σ2(Fo2) + (0.0763P)2 + 0.1838P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.009
3304 reflectionsΔρmax = 0.19 e Å3
296 parametersΔρmin = −0.21 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0039 (10)

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N10.78945 (9)0.29250 (19)0.16925 (7)0.0550 (3)
C20.88353 (11)0.3157 (3)0.20243 (8)0.0585 (4)
H20.9306 (14)0.344 (3)0.1687 (10)0.071 (5)*
C30.92113 (10)0.3055 (2)0.28263 (8)0.0510 (3)
C40.85387 (10)0.26693 (18)0.32912 (7)0.0439 (3)
C50.75150 (10)0.24194 (18)0.29686 (8)0.0457 (3)
C60.67970 (11)0.2042 (2)0.34033 (9)0.0564 (4)
H60.6994 (13)0.196 (3)0.3971 (11)0.069 (5)*
C70.58263 (12)0.1830 (3)0.30423 (10)0.0684 (5)
H70.5303 (15)0.158 (3)0.3354 (11)0.080 (6)*
C80.55295 (12)0.1992 (3)0.22380 (10)0.0668 (4)
H80.4799 (16)0.183 (3)0.1986 (11)0.080 (6)*
C90.62098 (11)0.2358 (2)0.18026 (9)0.0564 (4)
C910.58623 (13)0.2559 (3)0.09412 (11)0.0790 (6)
F91A0.48893 (9)0.2321 (3)0.07127 (7)0.1234 (6)
F91B0.62834 (10)0.1319 (2)0.05506 (7)0.1118 (5)
F91C0.60642 (9)0.4282 (2)0.06897 (7)0.1051 (5)
C100.72299 (10)0.25735 (19)0.21521 (8)0.0474 (3)
N110.90552 (8)0.26236 (16)0.40374 (6)0.0451 (3)
H110.8790 (14)0.233 (2)0.4455 (11)0.065 (5)*
C121.00454 (10)0.2982 (2)0.40618 (8)0.0472 (3)
C131.01616 (10)0.3251 (2)0.33251 (8)0.0560 (4)
H131.0773 (14)0.354 (3)0.3175 (10)0.073 (5)*
C141.07851 (10)0.30124 (19)0.47970 (8)0.0469 (3)
C151.17510 (10)0.3653 (2)0.48185 (9)0.0557 (4)
H151.1925 (12)0.408 (3)0.4342 (10)0.067 (5)*
C161.24628 (11)0.3636 (2)0.54972 (9)0.0590 (4)
H161.3115 (14)0.409 (3)0.5519 (10)0.072 (5)*
C171.22347 (10)0.3006 (2)0.61766 (8)0.0528 (3)
C181.12861 (11)0.2388 (2)0.61730 (9)0.0547 (4)
H181.1117 (13)0.195 (2)0.6656 (11)0.064 (5)*
C191.05731 (10)0.2390 (2)0.54829 (8)0.0525 (3)
H190.9913 (14)0.193 (2)0.5499 (10)0.064 (5)*
O201.29904 (8)0.30707 (18)0.68177 (6)0.0660 (3)
C211.27720 (15)0.2604 (3)0.75398 (10)0.0669 (5)
H21A1.3371 (18)0.280 (3)0.7903 (13)0.090 (7)*
H21B1.2269 (17)0.345 (3)0.7653 (12)0.089 (6)*
H21C1.2575 (14)0.133 (3)0.7546 (11)0.078 (6)*
O1W0.81044 (9)0.12279 (19)0.51922 (6)0.0610 (3)
H1W10.7916 (17)0.165 (3)0.5623 (13)0.092 (7)*
H1W20.802 (2)0.008 (4)0.5170 (15)0.121 (10)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0483 (6)0.0776 (8)0.0393 (6)0.0045 (6)0.0100 (5)−0.0023 (5)
C20.0472 (7)0.0893 (11)0.0408 (7)0.0035 (7)0.0132 (6)0.0002 (7)
C30.0445 (7)0.0674 (8)0.0416 (7)0.0037 (6)0.0105 (5)−0.0016 (6)
C40.0430 (7)0.0504 (7)0.0378 (6)0.0029 (5)0.0077 (5)−0.0014 (5)
C50.0448 (7)0.0500 (7)0.0414 (7)0.0012 (5)0.0076 (5)−0.0008 (5)
C60.0491 (8)0.0735 (9)0.0463 (7)−0.0054 (7)0.0100 (6)0.0035 (7)
C70.0489 (8)0.0975 (12)0.0597 (9)−0.0095 (8)0.0143 (7)0.0046 (9)
C80.0443 (8)0.0930 (12)0.0600 (9)−0.0049 (8)0.0046 (7)−0.0004 (8)
C90.0463 (8)0.0711 (9)0.0487 (8)0.0016 (6)0.0043 (6)−0.0033 (6)
C910.0496 (9)0.1272 (17)0.0557 (10)−0.0007 (10)0.0016 (7)−0.0078 (10)
F91A0.0517 (6)0.2442 (19)0.0643 (7)−0.0149 (8)−0.0089 (5)0.0008 (8)
F91B0.0891 (8)0.1757 (14)0.0664 (6)−0.0034 (8)0.0080 (6)−0.0496 (8)
F91C0.0881 (8)0.1500 (12)0.0710 (7)0.0129 (8)0.0040 (6)0.0398 (8)
C100.0460 (7)0.0539 (7)0.0415 (7)0.0029 (5)0.0080 (6)−0.0027 (5)
N110.0421 (6)0.0557 (6)0.0369 (5)0.0007 (4)0.0074 (4)0.0000 (4)
C120.0403 (6)0.0557 (7)0.0446 (7)0.0039 (5)0.0068 (5)−0.0019 (5)
C130.0410 (7)0.0829 (10)0.0446 (7)0.0022 (7)0.0108 (6)0.0002 (7)
C140.0412 (7)0.0537 (7)0.0444 (7)0.0042 (5)0.0061 (5)−0.0023 (5)
C150.0445 (7)0.0705 (9)0.0514 (8)−0.0003 (6)0.0090 (6)0.0010 (7)
C160.0412 (7)0.0743 (10)0.0596 (8)−0.0019 (7)0.0069 (6)−0.0005 (7)
C170.0430 (7)0.0580 (8)0.0515 (7)0.0063 (6)−0.0022 (6)−0.0032 (6)
C180.0495 (8)0.0667 (9)0.0457 (8)0.0007 (6)0.0054 (6)0.0027 (6)
C190.0415 (7)0.0682 (9)0.0459 (7)−0.0012 (6)0.0057 (6)−0.0004 (6)
O200.0488 (6)0.0855 (8)0.0553 (6)0.0016 (5)−0.0065 (5)−0.0003 (5)
C210.0688 (11)0.0694 (11)0.0532 (9)0.0023 (8)−0.0063 (8)−0.0012 (8)
O1W0.0696 (7)0.0718 (8)0.0449 (5)−0.0025 (6)0.0199 (5)0.0002 (5)

Geometric parameters (Å, °)

N1—C21.3155 (19)N11—H110.92 (2)
N1—C101.3800 (18)C12—C131.3662 (19)
C2—C31.4061 (19)C12—C141.4707 (18)
C2—H21.00 (2)C13—H130.96 (2)
C3—C41.4004 (19)C14—C191.385 (2)
C3—C131.4210 (19)C14—C151.403 (2)
C4—N111.3601 (17)C15—C161.378 (2)
C4—C51.4170 (19)C15—H150.977 (18)
C5—C61.411 (2)C16—C171.386 (2)
C5—C101.4202 (19)C16—H160.950 (19)
C6—C71.363 (2)C17—O201.3663 (16)
C6—H60.987 (19)C17—C181.382 (2)
C7—C81.401 (2)C18—C191.394 (2)
C7—H71.02 (2)C18—H180.988 (19)
C8—C91.368 (2)C19—H190.977 (19)
C8—H81.02 (2)O20—C211.419 (2)
C9—C101.419 (2)C21—H21A0.94 (2)
C9—C911.506 (2)C21—H21B0.97 (2)
C91—F91B1.327 (2)C21—H21C0.94 (2)
C91—F91A1.328 (2)O1W—H1W10.91 (2)
C91—F91C1.344 (3)O1W—H1W20.82 (3)
N11—C121.3845 (17)
C2—N1—C10118.69 (12)C4—N11—H11124.9 (11)
N1—C2—C3123.77 (13)C12—N11—H11125.7 (11)
N1—C2—H2117.9 (10)C13—C12—N11108.67 (12)
C3—C2—H2118.3 (10)C13—C12—C14129.95 (13)
C4—C3—C2117.49 (13)N11—C12—C14121.38 (12)
C4—C3—C13107.18 (12)C12—C13—C3107.17 (12)
C2—C3—C13135.34 (14)C12—C13—H13126.2 (11)
N11—C4—C3107.71 (12)C3—C13—H13126.6 (11)
N11—C4—C5130.89 (12)C19—C14—C15117.58 (13)
C3—C4—C5121.39 (12)C19—C14—C12122.34 (12)
C6—C5—C4124.31 (13)C15—C14—C12120.07 (13)
C6—C5—C10120.15 (13)C16—C15—C14120.92 (14)
C4—C5—C10115.54 (12)C16—C15—H15119.7 (10)
C7—C6—C5120.19 (14)C14—C15—H15119.4 (10)
C7—C6—H6119.7 (11)C15—C16—C17120.54 (14)
C5—C6—H6120.1 (11)C15—C16—H16121.5 (11)
C6—C7—C8120.51 (15)C17—C16—H16117.9 (11)
C6—C7—H7120.5 (11)O20—C17—C18124.48 (14)
C8—C7—H7119.0 (11)O20—C17—C16115.81 (13)
C9—C8—C7120.52 (15)C18—C17—C16119.70 (13)
C9—C8—H8120.9 (12)C17—C18—C19119.43 (14)
C7—C8—H8118.6 (12)C17—C18—H18120.1 (11)
C8—C9—C10121.00 (14)C19—C18—H18120.5 (11)
C8—C9—C91119.11 (14)C14—C19—C18121.83 (14)
C10—C9—C91119.88 (14)C14—C19—H19120.8 (10)
F91B—C91—F91A106.84 (17)C18—C19—H19117.4 (10)
F91B—C91—F91C105.85 (17)C17—O20—C21117.95 (13)
F91A—C91—F91C106.47 (18)O20—C21—H21A104.7 (14)
F91B—C91—C9112.99 (17)O20—C21—H21B110.5 (13)
F91A—C91—C9111.93 (16)H21A—C21—H21B109.4 (17)
F91C—C91—C9112.29 (16)O20—C21—H21C110.6 (12)
N1—C10—C5123.12 (13)H21A—C21—H21C110.3 (17)
N1—C10—C9119.26 (13)H21B—C21—H21C111.1 (18)
C5—C10—C9117.63 (13)H1W1—O1W—H1W2107 (2)
C4—N11—C12109.27 (11)
C10—N1—C2—C30.5 (3)C8—C9—C10—N1179.42 (16)
N1—C2—C3—C40.5 (3)C91—C9—C10—N1−1.4 (2)
N1—C2—C3—C13−179.65 (17)C8—C9—C10—C5−0.8 (2)
C2—C3—C4—N11179.62 (13)C91—C9—C10—C5178.39 (15)
C13—C3—C4—N11−0.26 (16)C3—C4—N11—C120.29 (15)
C2—C3—C4—C5−1.0 (2)C5—C4—N11—C12−179.04 (13)
C13—C3—C4—C5179.15 (13)C4—N11—C12—C13−0.21 (16)
N11—C4—C5—C6−0.2 (2)C4—N11—C12—C14−179.70 (12)
C3—C4—C5—C6−179.49 (14)N11—C12—C13—C30.05 (17)
N11—C4—C5—C10179.70 (13)C14—C12—C13—C3179.47 (14)
C3—C4—C5—C100.45 (19)C4—C3—C13—C120.12 (17)
C4—C5—C6—C7179.73 (15)C2—C3—C13—C12−179.72 (18)
C10—C5—C6—C7−0.2 (2)C13—C12—C14—C19−168.59 (16)
C5—C6—C7—C8−0.3 (3)N11—C12—C14—C1910.8 (2)
C6—C7—C8—C90.2 (3)C13—C12—C14—C1510.1 (2)
C7—C8—C9—C100.3 (3)N11—C12—C14—C15−170.52 (13)
C7—C8—C9—C91−178.87 (18)C19—C14—C15—C160.8 (2)
C8—C9—C91—F91B−121.27 (19)C12—C14—C15—C16−177.96 (14)
C10—C9—C91—F91B59.5 (2)C14—C15—C16—C17−0.8 (2)
C8—C9—C91—F91A−0.6 (3)C15—C16—C17—O20−179.21 (14)
C10—C9—C91—F91A−179.81 (17)C15—C16—C17—C180.0 (2)
C8—C9—C91—F91C119.09 (18)O20—C17—C18—C19179.80 (14)
C10—C9—C91—F91C−60.1 (2)C16—C17—C18—C190.6 (2)
C2—N1—C10—C5−1.0 (2)C15—C14—C19—C18−0.1 (2)
C2—N1—C10—C9178.74 (15)C12—C14—C19—C18178.60 (13)
C6—C5—C10—N1−179.48 (14)C17—C18—C19—C14−0.6 (2)
C4—C5—C10—N10.6 (2)C18—C17—O20—C21−4.8 (2)
C6—C5—C10—C90.7 (2)C16—C17—O20—C21174.42 (15)
C4—C5—C10—C9−179.21 (12)

Hydrogen-bond geometry (Å, °)

CgA, CgB, CgD are the centroids of the C5–C9,C1C, N1,C2–C5,C1C and C14–C19 rings, respectively
D—H···AD—HH···AD···AD—H···A
C6—H6···O1W0.987 (19)2.42 (2)3.340 (2)155 (2)
N11—H11···O1W0.92 (2)1.94 (2)2.845 (2)167 (2)
C19—H19···O1W0.977 (19)2.49 (2)3.439 (2)164 (1)
C8—H8···O20i1.02 (2)2.45 (2)3.427 (2)160 (2)
O1W—H1W1···N1ii0.91 (2)1.93 (2)2.807 (2)161 (2)
C21—H21C···CgAiii0.94 (2)2.83 (2)3.550 (2)135 (2)
C21—H21B···CgBiv0.97 (2)2.72 (2)3.503 (2)138 (2)
O1W—H1W2···CgDiii0.82 (3)2.62 (3)3.310 (2)143 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2190).

References

  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst 26, 343-350.
  • Atwood, J. L., Hamada, F., Robinson, K. D., Orr, G. W. & Vincent, R. L. (1991). Nature (London), 349, 683–684.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Domenicano, A. (1988). Stereochemical Applications of Gas-Phase Electron Diffraction, edited by I. Hargittai & M. Hargittai, pp. 281–324. New York: VCH.
  • Dutkiewicz, G., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Kubicki, M. (2010). Acta Cryst. E66, o874. [PMC free article] [PubMed]
  • Fan, Z. & Chen, L. (1987). Acta Cryst. C43, 2206–2209.
  • Lynch, D. E. & McClenaghan, I. (2002). Acta Cryst. E58, o1150–o1151.
  • Lynch, D. E., McClenaghan, I. & Light, M. E. (2001). Acta Cryst. E57, o56–o57.
  • Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst.41, 466–470.
  • Oxford Diffraction (2009). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1989). Stereochemical Workstation Operation Manual Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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