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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 o2189
https://doi.org/10.1107/S1600536810028035

2,2′-(4-{[(E)-4-Meth­­oxy­benzyl­­idene]amino}­phenyl­imino)­di­ethanol

Xiaoju Liu,a Bingqin Yang,a* Mingjuan Wanga and Maxim V. Borzova

aKey Laboratory of Synthetic and Natural Chemistry of the Ministry of Education, College of Chemistry and Material Science, The North-West University of Xi'an, Taibai Bei Avenue 229, Xi'an 710069, Shaanxi Province, People's Republic of China
*Correspondence e-mail: yangbq@nwu.edu.cn

(Received 17 May 2010; accepted 14 July 2010; online 31 July 2010)

In the title compound, C18H22N2O3, the dihedral angle between the aromatic rings is 3.9 (2)°. Both H atoms of the hy­droxy groups are involved in inter­molecular O—H⋯O hydrogen bonding. In the crystal structure, this hydrogen bonding assembles mol­ecules into chains of 21 symmetry extending parallel to the b axis. The almost planar (within 0.09 and 0.06 Å) 4-CH3O–C6H4–CH=N–C6H4– groups are oriented outwards the twofold screw axis.

Related literature

For practical inter­est in Shiff bases of general type p-R′–C6H4–CH=N–C6H4–R′′-p in various areas, see: von König et al. (1982[König, A. von, Moll, F. & Rosenhahn, L. (1982). Photographic Material, Process for the Production Thereof and Process for Production of Photographic Images. US Patent 4358531.]); Haldavanekar et al. (2009[Haldavanekar, V., Prabhu, M., Dharmaraj, R. & Kankan, R. N. (2009). Process for Synthesis of Arformoterol. WO Patent 2009147383 A1.]); Ferlin et al. (2004[Ferlin, M. G., Dalla Via, L. & Gia, O. M. (2004). Bioorg. Med. Chem. 12, 771-777.]); Lewis et al. (2009[Lewis, J., Matteucci, M., Chen, T. & Jiao, H. (2009). Hypoxia Activated Drugs of Nitrogen Mustard Alkylators as Anticancer Agents and Their Preparation. WO Patent 2009140553 A2.]). For the only two structurally characterized compounds of this type with R′′ = N(alk­yl)2, see: Nagao et al. (2002[Nagao, Y., Kimura, F., Kozawa, K. & Uchida, T. (2002). Shikizai Kyokaishi, 75, 415-420.]); Nakai et al. (1976[Nakai, H., Shiro, M., Emuzi, K., Sakata, S. & Kubota, T. (1976). Acta Cryst. B32, 1827-1833.]). For 4-[(E)-({4-[bis­(2-hy­droxy­eth­yl)amino]­phen­yl}imino)­meth­yl]phenol, C17H20N2O3, see: Liu et al. (2010[Liu, X., Yang, B. & Borzov, M. V. (2010). Acta Cryst. E66, o1646.]). For a description of preparation routines, see: Cho & Park (1997[Cho, Y. H. & Park, J. C. (1997). Tetrahedron Lett. 38, 8331-8334.]); Ferlin et al. (2004[Ferlin, M. G., Dalla Via, L. & Gia, O. M. (2004). Bioorg. Med. Chem. 12, 771-777.]); von König et al. (1982[König, A. von, Moll, F. & Rosenhahn, L. (1982). Photographic Material, Process for the Production Thereof and Process for Production of Photographic Images. US Patent 4358531.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • C18H22N2O3

  • Mr = 314.38

  • Monoclinic, P 21

  • a = 5.3795 (9) Å

  • b = 8.0585 (14) Å

  • c = 18.531 (3) Å

  • β = 91.168 (2)°

  • V = 803.2 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.24 × 0.13 × 0.07 mm
Data collection

  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (TWINABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.979, Tmax = 0.994

  • 4036 measured reflections

  • 1541 independent reflections

  • 1225 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.108

  • S = 1.06

  • 1541 reflections

  • 222 parameters

  • 1 restraint

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

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯O3i 0.95 (5) 1.84 (6) 2.762 (3) 177 (4)
O3—H3⋯O2ii 0.82 (4) 1.95 (4) 2.757 (4) 166 (4)
Symmetry codes: (i) x, y-1, z; (ii) [-x-1, y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXTL and OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810028035/im2204sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028035/im2204Isup2.hkl

checkCIF report


Comment top

Shiff bases of the general type p-R'–C6H4–CH=N–C6H4–R"-p are well-known compounds that find 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-hydroxy-ethyl)-{4-[(benzylidene)-amino]-phenyl}-amino)-ethanols as intermediates for their further conversion into paracyclophanes. This way, 2-((2-hydroxy-ethyl)-{4-[((1E)4-methoxy-benzylidene)-amino]-phenyl}-amino)-ethanol , C18H22N2O3, (I), and 4-({(E)-4-[bis-(2-hydroxy-ethyl)-amino]-phenylimino}-methyl)-phenol , C17H20N2O3, [II; Liu et al. (2010)] were prepared by a condensation reaction between 2-[(4-Amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol and 4-methoxy- or 4-hydroxybenzaldehyde, respectively.

Despite of the fact that structurally characterized Shiff 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 its sister compound [II; Liu et al. (2010)] show almost identical geometries (see Supplementary material). Bond lengths and angles as well as the C4–C7–N1–C8 torsion angle match well with the reported average 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/C18 and C8—C13/N2/C14/C16 are almost planar [within 0.09 and 0.06 Å]. The amino N2 atom is also in a planar environment [sum of the valent angles 359.9 (3)°] which most frequenty the case for aryldialkylamines (range from 317.6 to 360.0°, average value 359.0°).

In (I), both hydroxy H-atoms are involved into hydrogen bonding [for the H-bonds lengths and angles values, see the Table]. In (I), molecules along with their equivalents generated by a 21 screw axis form a one-dimensional infinite chain stretched along the b-axis. Organic moieties are oriented outwards the corresponding screw axis (see Fig. 2). These one-dimensional assemblies do not interact with their equivalent neighbours by any hydrogen bonds and are just stacked one by another. This results in an evident flattening of the entire CH3O—C6H4C(H)=NC6H4 moieties for the inter-chain repulsion diminishing. Crystal lattice packing of (I) differs markedly from that of (II) (Liu et al., 2010)).

Related literature top

For practical interest in Shiff bases of general type p-R'–C6H4–CH=N–C6H4–R"-p in various areas, see: von König et al. (1982); Haldavanekar et al. (2009); Ferlin et al. (2004); Lewis et al. (2009). For the only two structurally characterized compounds of this type with R" = N(alkyl)2, see: Nagao et al. (2002); Nakai et al. (1976). For 4-[(E)-({4-[bis(2-hydroxyethyl)amino]phenyl}imino)methyl]phenol, C17H20N2O3, see: Liu et al. (2010). For a description of preparation routines, see: Cho & Park (1997); Ferlin et al. (2004); von König et al. (1982). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

1-Chloro-4-nitrobenzene, 4-methoxy-benzaldehyde, 2-(2-hydroxy-ethylamino)-ethanol, ammonium formate, 10% Pd/C catalyst and solvents were purchased from Sinopharm Chemical Reagent and Tianjin Fuyu Chemical companies. 2-[(2-Hydroxy-ethyl)-(4-nitro-phenyl)-amino]-ethanol 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 by a modification of the procedure reported by von König et al. (1982).

Procedure: 1-chloro-4-nitrobenzene (15.76 g, 0.10 mol) was dissolved in 2-(2-hydroxy-ethylamino)-ethanol (50 ml). The reaction mixture was heated to 393 K for 10 h and then cooled down to room temperature. Precipitating crude 2-[(2-Hydroxy-ethyl)-(4-nitro-phenyl)-amino]-ethanol was filtered off, dried in vacuum and recrystallized from a minimal amount of hot ethanol. Yield 11.54 g (51%). 2-[(2-Hydroxy-ethyl)-(4-nitro-phenyl)-amino]-ethanol (8.15 g, 0.036 mol) was then 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-methoxybenzaldehyde (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 yellow solid was collected by filtration, washed with water, dried under reduced pressure and, finally, re-crystallized by a slow evaporation of its methanolic solution in air at 293 K. Yield 95%, m.p. 402 K. 1H NMR (I) δ: 8.50 (s, 1 H, CH═N), 6.78–7.83 (m, 8 H, C6H4), 3.31, 3.72 (both t, 4 H and 4 H, 3JHH = 7.2 Hz, CH2), 3.86 (s, 3H, CH3). A ingle crystal of (I) suitable for X-ray diffraction analysis was picked up directly from the obtained material.

Refinement top

All non-H atoms were refined anisotropically. H atoms except of H7 and OH were treated as riding atoms with distances of C—H = 0.96 (CH3), 0.97 (CH2), 0.93 Å (CArH), and Uiso(H) = 1.5 Ueq(C), 1.2 Ueq(C), and 1.2 Ueq(C), respectively. Atoms H7 and OH hydrogen atoms were found from difference Fourier syntheses and refined isotropically. Despite the fact that an achiral compound (I) crystallizes in a chiral space group P21, neither the absolute structure determination nor approval of the inversion twinning was possible due to evident reasons (Mo-Kα radiation with no atoms heavier than oxygen) and the refinement for (I) was preformed with the Friedel opposites merged (MERG 3 instruction).

Structure description top

Shiff bases of the general type p-R'–C6H4–CH=N–C6H4–R"-p are well-known compounds that find 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-hydroxy-ethyl)-{4-[(benzylidene)-amino]-phenyl}-amino)-ethanols as intermediates for their further conversion into paracyclophanes. This way, 2-((2-hydroxy-ethyl)-{4-[((1E)4-methoxy-benzylidene)-amino]-phenyl}-amino)-ethanol , C18H22N2O3, (I), and 4-({(E)-4-[bis-(2-hydroxy-ethyl)-amino]-phenylimino}-methyl)-phenol , C17H20N2O3, [II; Liu et al. (2010)] were prepared by a condensation reaction between 2-[(4-Amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol and 4-methoxy- or 4-hydroxybenzaldehyde, respectively.

Despite of the fact that structurally characterized Shiff 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 its sister compound [II; Liu et al. (2010)] show almost identical geometries (see Supplementary material). Bond lengths and angles as well as the C4–C7–N1–C8 torsion angle match well with the reported average 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/C18 and C8—C13/N2/C14/C16 are almost planar [within 0.09 and 0.06 Å]. The amino N2 atom is also in a planar environment [sum of the valent angles 359.9 (3)°] which most frequenty the case for aryldialkylamines (range from 317.6 to 360.0°, average value 359.0°).

In (I), both hydroxy H-atoms are involved into hydrogen bonding [for the H-bonds lengths and angles values, see the Table]. In (I), molecules along with their equivalents generated by a 21 screw axis form a one-dimensional infinite chain stretched along the b-axis. Organic moieties are oriented outwards the corresponding screw axis (see Fig. 2). These one-dimensional assemblies do not interact with their equivalent neighbours by any hydrogen bonds and are just stacked one by another. This results in an evident flattening of the entire CH3O—C6H4C(H)=NC6H4 moieties for the inter-chain repulsion diminishing. Crystal lattice packing of (I) differs markedly from that of (II) (Liu et al., 2010)).

For practical interest in Shiff bases of general type p-R'–C6H4–CH=N–C6H4–R"-p in various areas, see: von König et al. (1982); Haldavanekar et al. (2009); Ferlin et al. (2004); Lewis et al. (2009). For the only two structurally characterized compounds of this type with R" = N(alkyl)2, see: Nagao et al. (2002); Nakai et al. (1976). For 4-[(E)-({4-[bis(2-hydroxyethyl)amino]phenyl}imino)methyl]phenol, C17H20N2O3, see: Liu et al. (2010). For a description of preparation routines, see: Cho & Park (1997); Ferlin et al. (2004); von König et al. (1982). For a description of the Cambridge Structural Database, see: Allen (2002).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXTL97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. Asymmetric unit of (I) showing the labelling scheme and thermal ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. View of a 21-symmetrical chain assembled by molecules of (I) via hydrogen bonds. 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. 2-fold screw axis is depicted as a long-dash line.
2,2'-(4-{[(E)-4-Methoxybenzylidene]amino}phenylimino)diethanol top
Crystal data top
C18H22N2O3F(000) = 336
Mr = 314.38Dx = 1.300 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2324 reflections
a = 5.3795 (9) Åθ = 2.0–28.2°
b = 8.0585 (14) ŵ = 0.09 mm−1
c = 18.531 (3) ÅT = 296 K
β = 91.168 (2)°Block, yellow
V = 803.2 (2) Å30.24 × 0.13 × 0.07 mm
Z = 2
Data collection top
Bruker SMART APEXII
diffractometer		1541 independent reflections
Radiation source: fine-focus sealed tube1225 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 8.333 pixels mm-1θmax = 25.1°, θmin = 2.2°
phi and ω scansh = −5→6
Absorption correction: multi-scan
(TWINABS; Sheldrick, 1996)		k = −9→9
Tmin = 0.979, Tmax = 0.994l = −22→20
4036 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0702P)2]
where P = (Fo2 + 2Fc2)/3'
S = 1.06(Δ/σ)max < 0.001
1541 reflectionsΔρmax = 0.17 e Å−3
222 parametersΔρmin = −0.13 e Å−3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.028 (7)
Crystal data top
C18H22N2O3V = 803.2 (2) Å3
Mr = 314.38Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.3795 (9) ŵ = 0.09 mm−1
b = 8.0585 (14) ÅT = 296 K
c = 18.531 (3) Å0.24 × 0.13 × 0.07 mm
β = 91.168 (2)°
Data collection top
Bruker SMART APEXII
diffractometer		1541 independent reflections
Absorption correction: multi-scan
(TWINABS; Sheldrick, 1996)		1225 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.994Rint = 0.037
4036 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.17 e Å−3
1541 reflectionsΔρmin = −0.13 e Å−3
222 parameters
Special details top

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 F^2^ 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
O10.5558 (4)0.2396 (3)−0.24985 (10)0.0589 (6)
O2−0.3959 (5)−0.0877 (3)0.43576 (14)0.0712 (8)
O3−0.4849 (5)0.5749 (3)0.43870 (13)0.0628 (7)
N10.1089 (5)0.2496 (3)0.06704 (12)0.0469 (6)
N2−0.1774 (5)0.2079 (3)0.35822 (11)0.0515 (7)
C10.5101 (5)0.2264 (4)−0.17743 (13)0.0424 (7)
C20.6533 (6)0.1361 (4)−0.12960 (15)0.0485 (7)
H2A0.79470.0811−0.14500.058*
C30.5840 (6)0.1278 (4)−0.05799 (15)0.0476 (7)
H3A0.68300.0680−0.02550.057*
C40.3737 (6)0.2052 (4)−0.03335 (14)0.0427 (7)
C50.2341 (5)0.3012 (4)−0.08283 (14)0.0466 (7)
H50.09390.3577−0.06750.056*
C60.3029 (6)0.3123 (4)−0.15342 (15)0.0487 (8)
H60.21060.3776−0.18550.058*
C70.3019 (6)0.1862 (4)0.04166 (16)0.0494 (8)
C80.0474 (5)0.2305 (4)0.14073 (14)0.0416 (7)
C90.1730 (6)0.1309 (4)0.19122 (15)0.0471 (7)
H90.30950.06920.17690.057*
C100.0986 (5)0.1223 (4)0.26191 (15)0.0434 (7)
H100.18490.05370.29400.052*
C11−0.1033 (5)0.2140 (3)0.28648 (14)0.0405 (7)
C12−0.2278 (5)0.3138 (4)0.23556 (14)0.0474 (7)
H12−0.36250.37740.24980.057*
C13−0.1543 (5)0.3197 (4)0.16480 (14)0.0478 (7)
H13−0.24320.38570.13220.057*
C14−0.0579 (6)0.0964 (4)0.40875 (15)0.0508 (8)
H14B−0.08000.13880.45720.061*
H14A0.11900.09520.39970.061*
C15−0.1541 (6)−0.0790 (4)0.40534 (16)0.0562 (8)
H15A−0.1624−0.11580.35550.067*
H15B−0.0413−0.15190.43180.067*
C16−0.3805 (6)0.3088 (4)0.38402 (15)0.0488 (8)
H16B−0.45160.25600.42590.059*
H16A−0.50920.31580.34670.059*
C17−0.2951 (6)0.4822 (4)0.40415 (17)0.0547 (8)
H17B−0.15080.47470.43620.066*
H17A−0.24570.54030.36090.066*
C180.7676 (6)0.1549 (5)−0.27577 (17)0.0647 (10)
H18C0.77390.1667−0.32730.097*
H18A0.75670.0394−0.26360.097*
H18B0.91540.2013−0.25400.097*
H2−0.428 (9)−0.200 (7)0.438 (2)0.116 (18)*
H3−0.542 (8)0.522 (6)0.473 (2)0.094 (16)*
H70.417 (7)0.122 (5)0.072 (2)0.070 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0670 (15)0.0725 (15)0.0376 (10)0.0002 (13)0.0076 (10)0.0024 (11)
O20.0969 (19)0.0440 (14)0.0745 (16)−0.0085 (13)0.0465 (14)−0.0068 (12)
O30.1009 (19)0.0386 (12)0.0500 (13)0.0089 (12)0.0287 (12)0.0006 (11)
N10.0500 (15)0.0515 (15)0.0395 (12)0.0011 (13)0.0089 (11)−0.0011 (12)
N20.0741 (18)0.0424 (14)0.0388 (13)0.0072 (14)0.0176 (12)0.0014 (11)
C10.0462 (17)0.0451 (16)0.0362 (14)−0.0077 (15)0.0069 (12)−0.0046 (14)
C20.0472 (17)0.0520 (18)0.0469 (16)0.0042 (15)0.0118 (13)−0.0010 (15)
C30.0505 (17)0.0494 (18)0.0431 (16)0.0040 (15)0.0041 (13)0.0035 (14)
C40.0463 (17)0.0440 (18)0.0380 (14)−0.0032 (14)0.0044 (12)−0.0022 (13)
C50.0446 (16)0.0497 (18)0.0454 (16)0.0039 (15)0.0030 (13)−0.0061 (14)
C60.0501 (17)0.0525 (18)0.0431 (15)0.0013 (16)−0.0041 (13)0.0026 (15)
C70.055 (2)0.053 (2)0.0408 (16)0.0006 (17)0.0054 (15)−0.0003 (14)
C80.0459 (16)0.0408 (16)0.0384 (14)−0.0046 (14)0.0062 (12)−0.0015 (14)
C90.0505 (17)0.0436 (17)0.0477 (16)0.0027 (15)0.0124 (13)−0.0021 (14)
C100.0499 (17)0.0405 (16)0.0400 (15)0.0022 (14)0.0063 (13)0.0026 (13)
C110.0524 (18)0.0319 (15)0.0375 (14)−0.0050 (13)0.0077 (12)−0.0007 (12)
C120.0472 (17)0.0478 (17)0.0477 (16)0.0060 (15)0.0129 (13)−0.0021 (15)
C130.0499 (18)0.0497 (17)0.0439 (16)0.0055 (16)0.0029 (13)0.0042 (15)
C140.0660 (19)0.0506 (19)0.0360 (14)−0.0014 (16)0.0083 (13)0.0003 (14)
C150.074 (2)0.0450 (18)0.0506 (17)0.0049 (17)0.0215 (15)0.0067 (15)
C160.064 (2)0.0413 (17)0.0423 (15)−0.0047 (15)0.0172 (14)−0.0018 (14)
C170.074 (2)0.0420 (17)0.0483 (16)−0.0061 (16)0.0156 (15)−0.0042 (14)
C180.063 (2)0.084 (3)0.0475 (18)−0.010 (2)0.0156 (16)−0.0099 (18)
Geometric parameters (Å, º) top
O1—C11.373 (3)C8—C131.383 (4)
O1—C181.420 (4)C8—C91.396 (4)
O2—C151.430 (4)C9—C101.379 (4)
O2—H20.92 (5)C9—H90.9300
O3—C171.427 (4)C10—C111.398 (4)
O3—H30.82 (5)C10—H100.9300
N1—C71.257 (4)C11—C121.400 (4)
N1—C81.420 (3)C12—C131.378 (4)
N2—C111.397 (3)C12—H120.9300
N2—C141.440 (4)C13—H130.9300
N2—C161.451 (4)C14—C151.506 (5)
C1—C21.372 (4)C14—H14B0.9700
C1—C61.393 (4)C14—H14A0.9700
C2—C31.387 (4)C15—H15A0.9700
C2—H2A0.9300C15—H15B0.9700
C3—C41.378 (4)C16—C171.515 (4)
C3—H3A0.9300C16—H16B0.9700
C4—C51.405 (4)C16—H16A0.9700
C4—C71.458 (4)C17—H17B0.9700
C5—C61.369 (4)C17—H17A0.9700
C5—H50.9300C18—H18C0.9600
C6—H60.9300C18—H18A0.9600
C7—H70.98 (4)C18—H18B0.9600
C1—O1—C18117.0 (2)N2—C11—C12121.3 (2)
C15—O2—H2104 (3)C10—C11—C12116.6 (2)
C17—O3—H3111 (3)C13—C12—C11121.2 (3)
C7—N1—C8121.7 (3)C13—C12—H12119.4
C11—N2—C14120.6 (2)C11—C12—H12119.4
C11—N2—C16121.7 (2)C12—C13—C8122.1 (3)
C14—N2—C16117.7 (2)C12—C13—H13119.0
C2—C1—O1124.3 (3)C8—C13—H13119.0
C2—C1—C6120.0 (2)N2—C14—C15114.2 (3)
O1—C1—C6115.7 (2)N2—C14—H14B108.7
C1—C2—C3119.0 (3)C15—C14—H14B108.7
C1—C2—H2A120.5N2—C14—H14A108.7
C3—C2—H2A120.5C15—C14—H14A108.7
C4—C3—C2122.2 (3)H14B—C14—H14A107.6
C4—C3—H3A118.9O2—C15—C14110.1 (3)
C2—C3—H3A118.9O2—C15—H15A109.6
C3—C4—C5117.7 (2)C14—C15—H15A109.6
C3—C4—C7120.2 (3)O2—C15—H15B109.6
C5—C4—C7122.1 (3)C14—C15—H15B109.6
C6—C5—C4120.5 (3)H15A—C15—H15B108.1
C6—C5—H5119.7N2—C16—C17111.8 (3)
C4—C5—H5119.7N2—C16—H16B109.3
C5—C6—C1120.4 (3)C17—C16—H16B109.3
C5—C6—H6119.8N2—C16—H16A109.3
C1—C6—H6119.8C17—C16—H16A109.3
N1—C7—C4123.4 (3)H16B—C16—H16A107.9
N1—C7—H7121 (2)O3—C17—C16112.2 (3)
C4—C7—H7115 (2)O3—C17—H17B109.2
C13—C8—C9117.0 (2)C16—C17—H17B109.2
C13—C8—N1117.0 (3)O3—C17—H17A109.2
C9—C8—N1126.0 (3)C16—C17—H17A109.2
C10—C9—C8121.3 (3)H17B—C17—H17A107.9
C10—C9—H9119.4O1—C18—H18C109.5
C8—C9—H9119.4O1—C18—H18A109.5
C9—C10—C11121.7 (3)H18C—C18—H18A109.5
C9—C10—H10119.2O1—C18—H18B109.5
C11—C10—H10119.2H18C—C18—H18B109.5
N2—C11—C10122.0 (3)H18A—C18—H18B109.5
C18—O1—C1—C2−0.8 (4)C8—C9—C10—C11−0.8 (5)
C18—O1—C1—C6179.3 (3)C14—N2—C11—C10−4.5 (4)
O1—C1—C2—C3−178.0 (3)C16—N2—C11—C10177.3 (3)
C6—C1—C2—C31.9 (5)C14—N2—C11—C12175.9 (3)
C1—C2—C3—C41.1 (5)C16—N2—C11—C12−2.3 (4)
C2—C3—C4—C5−3.0 (5)C9—C10—C11—N2−179.0 (3)
C2—C3—C4—C7177.0 (3)C9—C10—C11—C120.6 (4)
C3—C4—C5—C61.9 (4)N2—C11—C12—C13−180.0 (3)
C7—C4—C5—C6−178.0 (3)C10—C11—C12—C130.4 (4)
C4—C5—C6—C11.0 (4)C11—C12—C13—C8−1.2 (5)
C2—C1—C6—C5−3.0 (5)C9—C8—C13—C121.0 (4)
O1—C1—C6—C5177.0 (3)N1—C8—C13—C12−178.5 (3)
C8—N1—C7—C4−179.0 (3)C11—N2—C14—C15−81.9 (3)
C3—C4—C7—N1−178.0 (3)C16—N2—C14—C1596.3 (3)
C5—C4—C7—N11.9 (5)N2—C14—C15—O2−72.9 (3)
C7—N1—C8—C13173.3 (3)C11—N2—C16—C17−83.9 (3)
C7—N1—C8—C9−6.2 (5)C14—N2—C16—C1797.9 (3)
C13—C8—C9—C100.0 (4)N2—C16—C17—O3−172.0 (2)
N1—C8—C9—C10179.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.95 (5)1.84 (6)2.762 (3)177 (4)
O3—H3···O2ii0.82 (4)1.95 (4)2.757 (4)166 (4)
Symmetry codes: (i) x, y−1, z; (ii) −x−1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC18H22N2O3
Mr314.38
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)5.3795 (9), 8.0585 (14), 18.531 (3)
β (°) 91.168 (2)
V (Å3)803.2 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.24 × 0.13 × 0.07
Data collection
DiffractometerBruker SMART APEXII
Absorption correctionMulti-scan
(TWINABS; Sheldrick, 1996)
Tmin, Tmax0.979, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections		4036, 1541, 1225
Rint0.037
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.108, 1.06
No. of reflections1541
No. of parameters222
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.17, −0.13

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009), SHELXTL97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.95 (5)1.84 (6)2.762 (3)177 (4)
O3—H3···O2ii0.82 (4)1.95 (4)2.757 (4)166 (4)
Symmetry codes: (i) x, y−1, z; (ii) −x−1, y+1/2, −z+1.
 

Acknowledgements

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.

References

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o2189
https://doi.org/10.1107/S1600536810028035
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