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 July 1; 66(Pt 7): o1646.
Published online 2010 June 16. doi:  10.1107/S1600536810021926
PMCID: PMC3006715

4-[(E)-({4-[Bis­(2-hy­droxy­eth­yl)amino]­phen­yl}imino)­meth­yl]phenol

Abstract

In the title compound, C17H20N2O3, the amino N atom is in a planar environment (sum of angles = 360.0°). All hy­droxy H atoms are involved in hydrogen bonding. In the crystal structure, two O—H(...)O and an O—H(...)Nimino hydrogen bond result in the formation of a three-dimensional network. The latter hydrogen bonding causes distortion of the planarity of the 4-HO–C6H4–CH=N–C6H4– fragment by rotation around the =N—CPh bond. The crystal studied was a non-merohedral twin [refined BASF parameter for the major component = 0.5293 (7)].

Related literature

For Schiff bases of the general type p-R′–C6H4–CH=N–C6H4R′′-p, see: von König et al. (1982 [triangle]); Haldavanekar et al. (2009 [triangle]); Ferlin et al. (2004 [triangle]); Lewis et al. (2009 [triangle]). For the only two structurally characterized compounds of the type with R′′ = N(alk­yl)2, see: Nagao et al. (2002 [triangle]); Nakai et al. (1976 [triangle]). For the structure of 2,2′-(4-{[(1E)-(4-meth­oxy­phen­yl)methyl­ene]amino}­phenyl­imino) bis­ethanol, see: Liu et al. (2010 [triangle]). For the preparation, see: Cho & Park (1997 [triangle]); Ferlin et al. (2004 [triangle]); von König et al. (1982 [triangle]). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1646-scheme1.jpg

Experimental

Crystal data

  • C17H20N2O3
  • M r = 300.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1646-efi1.jpg
  • a = 10.1426 (9) Å
  • b = 9.5192 (9) Å
  • c = 15.8600 (14) Å
  • β = 92.679 (1)°
  • V = 1529.6 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.36 × 0.27 × 0.13 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (TWINABS; Sheldrick, 1996 [triangle]) T min = 0.968, T max = 0.988
  • 5506 measured reflections
  • 5506 independent reflections
  • 2959 reflections with I > 2σ(I)

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.109
  • S = 0.84
  • 5506 reflections
  • 217 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; 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]) and OLEX2 (Dolomanov et al., 2009 [triangle]); software used to prepare material for publication: SHELXL97 and OLEX2.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021926/hg2687sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021926/hg2687Isup2.hkl

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

Acknowledgments

Financial support from the National Natural Science Foundation of China (project No. 20972125) is gratefully acknowledged. The authors are grateful to Mr Sun Wei for his help in measuring the 1H NMR spectra.

supplementary crystallographic information

Comment

Schiff bases of general type p-R'–C6H4–CH=N–C6H4–R"-p are well-known objects that find their practical application in various areas [photography (for instance, see von König et al., 1982), medicinal and pharmaceutical chemistry (for instance, see Haldavanekar et al., 2009; Ferlin et al., 2004; Lewis et al., 2009)]. Recently we were interested in preparation of a series of 2,2'-(4-{[(1E)-phenylmethylene]amino}phenylimino)bisethanols as semi-products for their further conversion into paracyclophanes. This way, 4-[(E)-({4-[bis(2-hydroxyethyl)amino]phenyl}imino)methyl]phenol, C17H20N2O3, (I), and 2,2'-(4-{[(1E)-(4-methoxyphenyl)methylene]amino}phenylimino)bisethanol, C18H22N2O3, [II; Liu et al. (2010)], were prepared by a condensation reaction between 2,2'-[(4-aminophenyl)imino]bisethanol and 4-methoxy- or 4-hydroxybenzaldehyde, respectively (see Scheme).

Despite of the fact that structurally characterized Schiff bases of general type p-R'–C6H4–CH=N–C6H4–R"-p are well presented in the Cambridge Structural Database [CSD; Version 5.27, release February 2009; Allen, 2002; 128 entries, 173 fragments], among them there are only two compounds with R" = N(alkyl)2 [namely: R' = H, R'' = NEt2 (Nagao et al., 2002) and R' = NO2, R" = NMe2 (Nakai et al., 1976)]. From this viewpoint, X-ray single crystal study of (I) presents a certain descriptive interest.

The asymmetric unit of (I) is shown in Fig. 1. Except of dihedral angle C7–N1–C8–C9, asymmetric units of (I) and [II; Liu et al. (2010)] have nearly identical geometries (Supplementary materials). Bond lengths, valency angles and C4–C7–N1–C8 torsion angle values for C4/C7/N1/C8 fragment match well the reported median values for p-R'–C6H4–CH=N–C6H4–R"-p [analysis of the Cambridge Structural Database (CSD); Version 5.27, release February 2009; Allen, 2002; 128 entries, 173 fragments]. Fragments O1/C1—C7/N1 and C8—C13/N2/C14/C16 are nearly planar [within 0.04 and 0.07 Å for (I)]. Atom N2 is also in a planar environment [sum of the valent angles 360.0 (6)°] what presents the most frequent case for aryldialkylamines (range from 317.6 to 360.0°, median value 359.0°)..

All hydroxy H-atoms in (I) are involved into hydrogen bonding [for the H-bonds lengths and angles values see the Table 1]. This way, O1—H1···O3 H-bonds assemble the molecules in chains stretched along the c-axis of the crystal lattice [linked molecules are connected by a simple (0,0,±1) translation]. These chains, in their turn, assemble into "foldered" zigzag layers parallel to the a0b face due to O2—H2···N1 bonds (see Fig. 2). Finally, O3—H3···O2 bonds join the adjacent layers what completes the entire 3D-framework (see Fig. 3). Involving of the N1 imino-atom into H-binding, evidently, causes a considerable distortion of the 4-HO–C6H4–CH=N–C6H4– fragment planarity by rotation around the ═N—CPh bond.

Experimental

1-Chloro-4-nitrobenzene, 4-methoxy- and 4-hydroxybenzaldehydes, 2,2'-iminobisethanol, ammonium formate, 10% Pd/C catalyst and solvents were purchased from Sinopharm Chemical Reagent and Tianjin Fuyu Chemical companies. 2,2'-[(4-nitrophenyl)imino]bisethanol was prepared as described by Cho & Park (1997) and Ferlin et al. (2004). Reduction of the nitro-group was carried out as described by Lewis et al. (2009). Schiff-base preparation was done closely to what described by von König et al. (1982). – 1H NMR spectra were recorded on a Varian INOVA-400 instrument in CD3OD at 298 K using the resonance of the residual solvent protons as an internal reference [δ(H) = 3.30 ppm]. Procedure: 1-chloro-4-nitrobenzene (15.76 g, 0.10 mol) was dissolved in 2,2'-iminobisethanol (50 ml). The reaction mixture was heated at 393 K for 10 h, cooled down to room temperature, the precipitated crude 2,2'-[(4-nitrophenyl)imino]bisethanol filtered off, dried in vacuum and recrystallized from minimal amount of hot ethanol. Yield 11.54 g (51%). 2,2'-[(4-nitrophenyl)imino]bisethanol (8.15 g, 0.036 mol) was dissolved in MeOH (50 ml). To this solution, HCOONH4 (0.216 mol) and 10% Pd/C (0.6 g) were added and the slurry was stirred at 293 K for 30 min. On removal of the catalyst by filtration, the filtrate was placed into a N2-flushed flask containing 1 ml of acetic acid and an equimolar (0.036 mol) amount of 4-hydroxybenzaldehyde (0.036 mol) was added dropwise at 333 K during 30 min. The reaction mixture was kept at the same temperature for additional 30 min, cooled down to 273 K and ice-cold water (200 ml) was added. The precipitated light-green (I) solid was collected by filtration, washed with water, dried under reduced pressure and, finally, re-crystallized by a slow evaporation of their methanol solutions in air at 293 K. Yield 92%, m.p. 476 K. 1H NMR for (I) δ: 8.45 (s, 1H, CH═N), 6.78–7.73 (m, 8H, C6H4), 3.30, 3.74 (both t, 4 H and 4 H, 3JHH = 7.2 Hz, CH2). Single crystal of (I) suitable for X-ray diffraction analysis was picked up directly from the obtained materials.

Refinement

All non-H atoms were refined anisotropically. H atoms except of H7 and OH group ones were treated as riding atoms with distances C—H = 0.97 (CH2), 0.93 Å (CArH), and Uiso(H) = 1.2Ueq(C). Atoms H7 and OH group H atoms were found from difference Fourier syntheses and refined isotropically.

Figures

Fig. 1.
Asymmetric unit of the compound (I) with labelling and thermal ellipsoids at the 50% probability level.
Fig. 2.
Assembling of the molecules of (I) into a "foldered" zigzag layer. Hydrogen atoms except of the OH ones are omitted for clarity. Labelling is provided only for atoms involved in H-bonding. H-bonds are depicted as dashed lines.
Fig. 3.
Inter-layer assembling of the molecules of (I) into a 3D-network. Hydrogen atoms except of the OH ones are omitted for clarity. Only O3—H3···O2iii [symmetry code: (iii) –x + 1.5, y + 0.5, –z + 0.5] bonds ...

Crystal data

C17H20N2O3F(000) = 640
Mr = 300.35Dx = 1.304 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4620 reflections
a = 10.1426 (9) Åθ = 2.3–27.0°
b = 9.5192 (9) ŵ = 0.09 mm1
c = 15.8600 (14) ÅT = 296 K
β = 92.679 (1)°Block, green
V = 1529.6 (2) Å30.36 × 0.27 × 0.13 mm
Z = 4

Data collection

Bruker SMART APEXII diffractometer5506 measured reflections
Radiation source: fine-focus sealed tube5506 independent reflections
graphite2959 reflections with I > 2σ(I)
Detector resolution: 8.333 pixels mm-1θmax = 25.1°, θmin = 2.3°
phi and ω scansh = −12→12
Absorption correction: multi-scan (TWINABS; Sheldrick, 1996)k = 0→11
Tmin = 0.968, Tmax = 0.988l = 0→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109w = 1/[σ2(Fo2) + (0.0702P)2] where P = (Fo2 + 2Fc2)/3
S = 0.84(Δ/σ)max < 0.001
5506 reflectionsΔρmax = 0.16 e Å3
217 parametersΔρmin = −0.18 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: 0.0107 (15)

Special details

Experimental. Sample of (I) was a two-component non-merohedral twin with approximately equal component contribution. Thus, the structure of (I) was solved and pre-refined for one of the components (HKLF 4 format) and finally refined for the full set of reflexions (HKLF 5 file format). The refined BASF parameter for the prevailing component equals 0.5293 (7).
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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
O10.84481 (15)0.10572 (15)1.16972 (7)0.0735 (5)
O20.56639 (11)0.06213 (12)0.32409 (7)0.0477 (3)
O30.90811 (13)0.32742 (15)0.26638 (8)0.0649 (4)
N10.89456 (12)0.22592 (15)0.77116 (8)0.0438 (4)
N20.89798 (12)0.13765 (13)0.41928 (7)0.0423 (4)
C10.84745 (17)0.11819 (19)1.08463 (10)0.0479 (5)
C20.80262 (17)0.00647 (18)1.03658 (10)0.0551 (5)
H2A0.7703−0.07301.06280.066*
C30.80526 (16)0.01135 (18)0.94979 (10)0.0505 (5)
H3A0.7768−0.06610.91810.061*
C40.84966 (15)0.12981 (17)0.90899 (9)0.0394 (4)
C50.89081 (15)0.24390 (17)0.95828 (9)0.0434 (4)
H50.91830.32560.93220.052*
C60.89162 (15)0.23798 (17)1.04515 (9)0.0443 (4)
H60.92180.31431.07720.053*
C70.85321 (16)0.1266 (2)0.81716 (10)0.0442 (4)
C80.88878 (15)0.20652 (16)0.68171 (9)0.0401 (4)
C90.78712 (16)0.13679 (17)0.63799 (9)0.0444 (4)
H90.71670.10250.66730.053*
C100.78819 (16)0.11715 (17)0.55179 (9)0.0452 (4)
H100.71750.07150.52420.054*
C110.89302 (15)0.16422 (16)0.50488 (9)0.0385 (4)
C120.99168 (16)0.24157 (17)0.54925 (9)0.0449 (4)
H121.06030.28020.52010.054*
C130.98867 (16)0.26125 (17)0.63517 (9)0.0450 (4)
H131.05570.31280.66270.054*
C140.79307 (15)0.05868 (17)0.37522 (9)0.0433 (4)
H14B0.7674−0.01920.41030.052*
H14A0.82580.02020.32360.052*
C150.67400 (15)0.14873 (17)0.35403 (10)0.0442 (4)
H15B0.64940.19980.40380.053*
H15A0.69480.21660.31100.053*
C161.01067 (15)0.17981 (18)0.37224 (10)0.0479 (5)
H16A1.02110.11300.32690.057*
H16B1.08920.17430.40940.057*
C171.00283 (17)0.32486 (19)0.33494 (10)0.0536 (5)
H17A0.97820.39160.37770.064*
H17B1.08850.35190.31550.064*
H10.880 (2)0.183 (2)1.1930 (13)0.107 (9)*
H20.5011 (18)0.130 (2)0.3071 (11)0.086 (7)*
H30.913 (2)0.408 (2)0.2387 (13)0.117 (9)*
H70.8211 (14)0.0378 (16)0.7921 (9)0.050 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.1199 (13)0.0705 (11)0.0296 (8)−0.0099 (9)−0.0027 (7)0.0057 (7)
O20.0524 (8)0.0448 (8)0.0442 (7)0.0026 (7)−0.0141 (6)−0.0081 (6)
O30.0834 (10)0.0586 (9)0.0499 (8)−0.0142 (8)−0.0269 (7)0.0155 (7)
N10.0480 (9)0.0525 (10)0.0303 (8)−0.0016 (7)−0.0057 (6)0.0003 (7)
N20.0449 (8)0.0523 (9)0.0290 (8)−0.0043 (7)−0.0030 (7)0.0018 (6)
C10.0604 (12)0.0515 (12)0.0314 (10)0.0057 (10)−0.0029 (9)0.0022 (8)
C20.0775 (13)0.0447 (12)0.0430 (11)−0.0039 (10)0.0006 (10)0.0081 (9)
C30.0674 (13)0.0429 (11)0.0406 (11)−0.0041 (9)−0.0050 (9)−0.0011 (8)
C40.0432 (10)0.0426 (10)0.0319 (9)0.0031 (8)−0.0042 (8)0.0015 (8)
C50.0492 (11)0.0445 (11)0.0365 (10)−0.0023 (9)0.0010 (8)0.0039 (8)
C60.0508 (11)0.0455 (11)0.0364 (10)−0.0008 (9)−0.0017 (8)−0.0056 (8)
C70.0466 (11)0.0480 (12)0.0373 (11)0.0008 (9)−0.0057 (8)−0.0017 (9)
C80.0452 (10)0.0437 (10)0.0307 (9)0.0000 (8)−0.0061 (8)0.0004 (8)
C90.0448 (10)0.0548 (11)0.0333 (10)−0.0069 (9)−0.0025 (8)0.0042 (8)
C100.0473 (10)0.0521 (11)0.0352 (10)−0.0096 (9)−0.0087 (8)0.0014 (8)
C110.0440 (10)0.0404 (10)0.0303 (9)0.0020 (8)−0.0073 (8)0.0050 (7)
C120.0445 (10)0.0555 (12)0.0343 (10)−0.0052 (9)−0.0036 (8)0.0060 (8)
C130.0456 (10)0.0515 (12)0.0370 (10)−0.0068 (9)−0.0092 (8)0.0010 (8)
C140.0521 (10)0.0451 (11)0.0318 (9)0.0012 (9)−0.0067 (8)−0.0011 (8)
C150.0486 (10)0.0451 (11)0.0383 (10)−0.0015 (9)−0.0066 (8)−0.0017 (8)
C160.0472 (10)0.0608 (12)0.0351 (10)0.0070 (9)−0.0035 (8)0.0014 (8)
C170.0553 (11)0.0654 (13)0.0392 (10)−0.0113 (10)−0.0088 (9)0.0078 (9)

Geometric parameters (Å, °)

O1—C11.3563 (18)C7—H70.984 (15)
O1—H10.89 (2)C8—C131.383 (2)
O2—C151.4310 (17)C8—C91.385 (2)
O2—H20.952 (19)C9—C101.3805 (19)
O3—C171.4172 (18)C9—H90.9300
O3—H30.89 (2)C10—C111.400 (2)
N1—C71.277 (2)C10—H100.9300
N1—C81.4292 (18)C11—C121.405 (2)
N2—C111.3843 (18)C12—C131.3773 (19)
N2—C161.4504 (18)C12—H120.9300
N2—C141.4546 (18)C13—H130.9300
C1—C21.373 (2)C14—C151.506 (2)
C1—C61.385 (2)C14—H14B0.9700
C2—C31.379 (2)C14—H14A0.9700
C2—H2A0.9300C15—H15B0.9700
C3—C41.386 (2)C15—H15A0.9700
C3—H3A0.9300C16—C171.503 (2)
C4—C51.391 (2)C16—H16A0.9700
C4—C71.459 (2)C16—H16B0.9700
C5—C61.3786 (19)C17—H17A0.9700
C5—H50.9300C17—H17B0.9700
C6—H60.9300
C1—O1—H1108.4 (14)C9—C10—H10119.2
C15—O2—H2102.4 (11)C11—C10—H10119.2
C17—O3—H3110.1 (14)N2—C11—C10121.75 (14)
C7—N1—C8118.17 (14)N2—C11—C12121.97 (14)
C11—N2—C16121.30 (13)C10—C11—C12116.28 (14)
C11—N2—C14120.41 (13)C13—C12—C11121.25 (15)
C16—N2—C14118.18 (12)C13—C12—H12119.4
O1—C1—C2117.58 (16)C11—C12—H12119.4
O1—C1—C6122.93 (16)C12—C13—C8121.84 (15)
C2—C1—C6119.49 (15)C12—C13—H13119.1
C1—C2—C3120.43 (16)C8—C13—H13119.1
C1—C2—H2A119.8N2—C14—C15111.96 (13)
C3—C2—H2A119.8N2—C14—H14B109.2
C2—C3—C4121.04 (16)C15—C14—H14B109.2
C2—C3—H3A119.5N2—C14—H14A109.2
C4—C3—H3A119.5C15—C14—H14A109.2
C3—C4—C5117.93 (14)H14B—C14—H14A107.9
C3—C4—C7118.23 (16)O2—C15—C14109.72 (13)
C5—C4—C7123.83 (15)O2—C15—H15B109.7
C6—C5—C4121.16 (15)C14—C15—H15B109.7
C6—C5—H5119.4O2—C15—H15A109.7
C4—C5—H5119.4C14—C15—H15A109.7
C5—C6—C1119.89 (15)H15B—C15—H15A108.2
C5—C6—H6120.1N2—C16—C17115.35 (14)
C1—C6—H6120.1N2—C16—H16A108.4
N1—C7—C4125.38 (17)C17—C16—H16A108.4
N1—C7—H7121.1 (8)N2—C16—H16B108.4
C4—C7—H7113.5 (8)C17—C16—H16B108.4
C13—C8—C9117.40 (14)H16A—C16—H16B107.5
C13—C8—N1118.95 (14)O3—C17—C16109.84 (14)
C9—C8—N1123.64 (14)O3—C17—H17A109.7
C10—C9—C8121.38 (15)C16—C17—H17A109.7
C10—C9—H9119.3O3—C17—H17B109.7
C8—C9—H9119.3C16—C17—H17B109.7
C9—C10—C11121.62 (15)H17A—C17—H17B108.2
O1—C1—C2—C3−178.64 (16)C16—N2—C11—C10−176.39 (14)
C6—C1—C2—C32.0 (3)C14—N2—C11—C10−0.2 (2)
C1—C2—C3—C4−1.7 (3)C16—N2—C11—C124.6 (2)
C2—C3—C4—C5−0.3 (2)C14—N2—C11—C12−179.19 (14)
C2—C3—C4—C7178.38 (16)C9—C10—C11—N2176.24 (14)
C3—C4—C5—C62.1 (2)C9—C10—C11—C12−4.7 (2)
C7—C4—C5—C6−176.54 (15)N2—C11—C12—C13−176.78 (14)
C4—C5—C6—C1−1.8 (2)C10—C11—C12—C134.1 (2)
O1—C1—C6—C5−179.58 (16)C11—C12—C13—C8−0.2 (2)
C2—C1—C6—C5−0.3 (2)C9—C8—C13—C12−3.3 (2)
C8—N1—C7—C4−178.79 (15)N1—C8—C13—C12177.43 (14)
C3—C4—C7—N1−178.17 (16)C11—N2—C14—C1579.93 (17)
C5—C4—C7—N10.5 (3)C16—N2—C14—C15−103.73 (15)
C7—N1—C8—C13−143.95 (16)N2—C14—C15—O2−170.21 (11)
C7—N1—C8—C936.9 (2)C11—N2—C16—C17−89.41 (17)
C13—C8—C9—C102.8 (2)C14—N2—C16—C1794.28 (17)
N1—C8—C9—C10−178.01 (14)N2—C16—C17—O3−71.61 (18)
C8—C9—C10—C111.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.89 (2)1.82 (2)2.669 (2)160 (2)
O2—H2···N1ii0.95 (2)1.82 (2)2.771 (2)172 (2)
O3—H3···O2iii0.89 (2)1.79 (2)2.674 (2)174 (2)

Symmetry codes: (i) x, y, z+1; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2687).

References

  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cho, Y. H. & Park, J. C. (1997). Tetrahedron Lett.38, 8331–8334.
  • Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst.42, 339–341.
  • Ferlin, M. G., Dalla Via, L. & Gia, O. M. (2004). Bioorg. Med. Chem.12, 771–777. [PubMed]
  • Haldavanekar, V., Prabhu, M., Dharmaraj, R. & Kankan, R. N. (2009). WO Patent 2009147383 A1.
  • König, A. von, Moll, F. & Rosenhahn, L. (1982). US Patent 4358531.
  • Lewis, J., Matteucci, M., Chen, T. & Jiao, H. (2009). WO Patent 2009140553 A2.
  • Liu, X., Yang, B., Wang, M. & Borzov, M. V. (2010). Acta Cryst E66 Submitted.
  • Nagao, Y., Kimura, F., Kozawa, K. & Uchida, T. (2002). Shikizai Kyokaishi, 75, 415–420.
  • Nakai, H., Shiro, M., Emuzi, K., Sakata, S. & Kubota, T. (1976). Acta Cryst. B32, 1827–1833.
  • Sheldrick, G. M. (1996). TWINABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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