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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1452–o1453.
Published online 2010 May 26. doi:  10.1107/S1600536810018891
PMCID: PMC2979590

4-(3,4-Dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-2-methoxy­phenol

Abstract

In the title compound, C18H21NO3, the oxazolidine ring adopts an envelope conformation with the N atom at the flap position. The two benzene rings make dihedral angles of 74.27 (14) and 73.26 (15)° with the mean plane through the oxazolidine ring. In the crystal structure, O—H(...)O and C—H(...)O hydrogen bonds connect adjacent mol­ecules into chains along [010] incorporating R 2 2(8) loops and further stabilization is provided by weak inter­molecular C—H(...)π inter­actions.

Related literature

For general background to and applications of the title oxazolidine compound, see: Fitzgerald et al. (2005 [triangle]); Kamat et al. (2000 [triangle]); Kumar et al. (2004 [triangle]); Walton et al. (2003 [triangle]). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 [triangle]). For a related structure, see: Duffy et al. (2004 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

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Object name is e-66-o1452-scheme1.jpg

Experimental

Crystal data

  • C18H21NO3
  • M r = 299.36
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1452-efi1.jpg
  • a = 7.8893 (6) Å
  • b = 11.7697 (9) Å
  • c = 17.4392 (13) Å
  • V = 1619.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 120 K
  • 0.31 × 0.15 × 0.15 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.975, T max = 0.987
  • 9140 measured reflections
  • 2131 independent reflections
  • 1622 reflections with I > 2σ(I)
  • R int = 0.067

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.096
  • S = 1.07
  • 2131 reflections
  • 206 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018891/hb5455sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018891/hb5455Isup2.hkl

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

Acknowledgments

This research was supported by Universiti Sains Malaysia (USM) under the University Research grant (No. 1001/PFARMASI/815004) and the Ministry of Science, Technology and Innovation through R&D Initiative Grant (311/IFN/692601). HKF and JHG thank USM for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). MRA gratefully acknowledges a PhD scholarship from Universiti Malaysia Sarawak. JHG also thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

4-Hydroxy-3-methoxybenzyldehyde has been used as a chemical intermediate in the production of pharmaceuticals and other chemicals. This compound is a widely used flavouring compound in food and personal products. The synthesis of new design chemical entity is part of the aim to produce pharmaceutical substances because the compound in the literature shown remarkable biological activities, such as anti-oxidant and anti-microbial properties (Fitzgerald et al., 2005; Kamat et al., 2000; Walton et al., 2003; Kumar et al., 2004). In this paper we report the full account of the structural data of the title oxazolidine compound, (I).

The title oxazolidine compound contains two aromatic phenyl rings bridged by an oxazolidine ring (Fig. 1). The oxazolidine ring with atom sequence C7/N1/C8/C9/O3 adopts an envolope conformation, with puckering parameters of Q = 0.421 (3) Å and [var phi] = 73.7 (3)°. The N1 atom is at the envelope flap position and it deviates from the least-square plane through the remaining four atoms by 0.634 (2) Å. The mean plane through the oxazolidine ring inclines at dihedral angles of 74.27 (14) and 73.26 (15)°, respectively, with the C1-C6 and C10-C15 phenyl rings. The bond lengths (Allen et al., 1987) and angles are within normal ranges and consistent to a closely related oxazolidine structure (Duffy et al., 2004).

In the crystal structure (Fig. 2), adjacent molecules are connected by intermolecular O1—H1O1···O3 and C5—H5A···O1 hydrogen bonds (Table 1) into one-dimensional chains along the [010] direction incorporating R22(8) hydrogen bond ring motifs (Bernstein et al., 1995). The crystal structure is further stabilized by weak intermolecular C16—H16A···Cg1 interactions (Table 1) involving the centroid of the C10-C15 phenyl ring.

Experimental

An anhydrous methanol solution of 4-hydroxy-3-methoxy-benzyldehyde (1.52 g, 10 mmol) was added to an anhydrous methanol solution of 2-methylamino-1-phenylpropan-1-ol (1.65 g, 10 mmol) and the reaction mixture was refluxed and stirred at 350 K for 8 h. The product was isolated and recrystallized from methanol and dried in vacuo to give colourless blocks of (I) in 80 % yield, which were washed three times with ethyl acetate and dried in a vacuum desiccator using CaCl2.

Refinement

Atom H1O1 was located from difference Fourier map and allowed to refine freely [O1—H1O1 = 0.92 (3) Å]. All other H atoms were placed in their calculated positions, with C—H = 0.93 – 0.98 Å, and refined using a riding model, with Uiso = 1.2 or 1.5 Ueq(C). A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The crystal structure of (I), viewed along the a axis, showing one-dimensional chains along the [010] direction. Hydrogen atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C18H21NO3F(000) = 640
Mr = 299.36Dx = 1.228 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2249 reflections
a = 7.8893 (6) Åθ = 2.3–30.0°
b = 11.7697 (9) ŵ = 0.08 mm1
c = 17.4392 (13) ÅT = 120 K
V = 1619.3 (2) Å3Block, colourless
Z = 40.31 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer2131 independent reflections
Radiation source: fine-focus sealed tube1622 reflections with I > 2σ(I)
graphiteRint = 0.067
[var phi] and ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −10→10
Tmin = 0.975, Tmax = 0.987k = −15→12
9140 measured reflectionsl = −22→20

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0389P)2 + 0.1539P] where P = (Fo2 + 2Fc2)/3
2131 reflections(Δ/σ)max < 0.001
206 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.21 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1)K.
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 > 2sigma(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
O10.6439 (2)−0.37357 (17)0.20663 (13)0.0265 (5)
O20.5613 (2)−0.21380 (16)0.30639 (11)0.0268 (5)
O30.2181 (2)0.07593 (15)0.14249 (11)0.0212 (4)
N10.0098 (3)−0.05656 (19)0.15472 (13)0.0233 (5)
C10.3559 (4)−0.2052 (2)0.08866 (16)0.0253 (7)
H1A0.3145−0.20430.03870.030*
C20.4683 (3)−0.2903 (2)0.11104 (17)0.0255 (6)
H2A0.4999−0.34670.07650.031*
C30.5324 (3)−0.2906 (2)0.18443 (17)0.0215 (6)
C40.4854 (3)−0.2053 (2)0.23596 (16)0.0206 (6)
C50.3704 (3)−0.1229 (2)0.21429 (16)0.0207 (6)
H5A0.3363−0.06780.24930.025*
C60.3054 (3)−0.1223 (2)0.13965 (16)0.0210 (6)
C70.1731 (3)−0.0363 (2)0.11753 (16)0.0203 (6)
H7A0.1583−0.03660.06170.024*
C8−0.0791 (3)0.0517 (2)0.14323 (17)0.0234 (6)
H8A−0.11360.05850.08940.028*
C90.0619 (3)0.1373 (2)0.16032 (15)0.0217 (6)
H9A0.06060.15470.21530.026*
C100.0490 (3)0.2465 (2)0.11626 (16)0.0204 (6)
C11−0.0056 (4)0.3445 (2)0.15220 (18)0.0284 (7)
H11A−0.02880.34350.20450.034*
C12−0.0263 (4)0.4449 (3)0.1110 (2)0.0365 (8)
H12A−0.06230.51050.13580.044*
C130.0064 (4)0.4468 (3)0.0336 (2)0.0355 (8)
H13A−0.00900.51340.00580.043*
C140.0625 (4)0.3493 (3)−0.00306 (18)0.0328 (7)
H14A0.08520.3504−0.05540.039*
C150.0844 (4)0.2504 (3)0.03850 (17)0.0264 (7)
H15A0.12360.18540.01390.032*
C160.5385 (4)−0.1212 (2)0.35869 (16)0.0275 (6)
H16A0.6074−0.13330.40330.041*
H16B0.4215−0.11690.37360.041*
H16C0.5713−0.05160.33420.041*
C17−0.0798 (4)−0.1538 (3)0.12300 (19)0.0343 (8)
H17A−0.0103−0.22040.12760.051*
H17C−0.1044−0.14020.06990.051*
H17D−0.1838−0.16510.15060.051*
C18−0.2325 (3)0.0658 (3)0.19449 (18)0.0320 (7)
H18A−0.31760.01140.18030.048*
H18D−0.27710.14120.18880.048*
H18B−0.20010.05380.24690.048*
H1O10.658 (4)−0.368 (3)0.259 (2)0.048 (10)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0250 (10)0.0216 (11)0.0331 (12)0.0061 (8)−0.0054 (9)−0.0006 (10)
O20.0282 (10)0.0223 (10)0.0299 (11)0.0039 (8)−0.0080 (9)−0.0025 (9)
O30.0145 (8)0.0178 (9)0.0314 (11)0.0008 (7)−0.0010 (8)−0.0004 (9)
N10.0171 (10)0.0220 (12)0.0309 (13)−0.0005 (10)0.0003 (10)0.0015 (11)
C10.0255 (14)0.0259 (15)0.0246 (16)−0.0010 (13)0.0001 (13)0.0009 (14)
C20.0257 (15)0.0193 (14)0.0316 (16)0.0008 (12)0.0024 (13)−0.0037 (13)
C30.0163 (13)0.0167 (13)0.0316 (16)−0.0010 (11)−0.0015 (12)0.0033 (13)
C40.0170 (13)0.0195 (13)0.0252 (15)−0.0042 (11)−0.0015 (11)0.0011 (13)
C50.0178 (12)0.0160 (14)0.0283 (15)−0.0010 (11)0.0025 (11)−0.0022 (13)
C60.0188 (13)0.0188 (14)0.0255 (15)−0.0039 (11)0.0013 (12)0.0027 (13)
C70.0190 (13)0.0176 (14)0.0243 (15)−0.0006 (11)−0.0014 (11)0.0003 (12)
C80.0180 (12)0.0246 (15)0.0274 (15)−0.0004 (12)−0.0017 (12)0.0051 (13)
C90.0179 (12)0.0240 (14)0.0233 (15)0.0037 (12)0.0014 (12)0.0006 (13)
C100.0110 (12)0.0238 (15)0.0263 (15)0.0001 (11)−0.0047 (11)−0.0001 (12)
C110.0229 (14)0.0284 (16)0.0339 (17)0.0034 (13)0.0024 (13)−0.0019 (14)
C120.0288 (17)0.0238 (17)0.057 (2)0.0078 (14)−0.0003 (16)−0.0010 (16)
C130.0293 (15)0.0245 (17)0.053 (2)0.0011 (15)−0.0081 (16)0.0161 (16)
C140.0293 (16)0.0375 (19)0.0315 (17)−0.0066 (15)−0.0048 (14)0.0086 (15)
C150.0249 (14)0.0245 (15)0.0298 (16)−0.0007 (13)−0.0014 (13)0.0012 (13)
C160.0293 (15)0.0271 (15)0.0259 (15)0.0059 (13)−0.0032 (13)−0.0018 (14)
C170.0235 (14)0.0289 (17)0.050 (2)−0.0086 (13)0.0014 (15)0.0005 (16)
C180.0220 (14)0.0352 (17)0.0389 (18)0.0019 (13)0.0051 (14)0.0042 (16)

Geometric parameters (Å, °)

O1—C31.370 (3)C9—C101.501 (4)
O1—H1O10.92 (3)C9—H9A0.9800
O2—C41.370 (3)C10—C111.382 (4)
O2—C161.432 (3)C10—C151.385 (4)
O3—C71.435 (3)C11—C121.393 (4)
O3—C91.462 (3)C11—H11A0.9300
N1—C171.455 (4)C12—C131.374 (5)
N1—C71.462 (3)C12—H12A0.9300
N1—C81.468 (3)C13—C141.386 (4)
C1—C61.379 (4)C13—H13A0.9300
C1—C21.394 (4)C14—C151.382 (4)
C1—H1A0.9300C14—H14A0.9300
C2—C31.376 (4)C15—H15A0.9300
C2—H2A0.9300C16—H16A0.9600
C3—C41.397 (4)C16—H16B0.9600
C4—C51.381 (4)C16—H16C0.9600
C5—C61.399 (4)C17—H17A0.9600
C5—H5A0.9300C17—H17C0.9600
C6—C71.505 (4)C17—H17D0.9600
C7—H7A0.9800C18—H18A0.9600
C8—C181.514 (4)C18—H18D0.9600
C8—C91.530 (4)C18—H18B0.9600
C8—H8A0.9800
C3—O1—H1O1108 (2)O3—C9—H9A108.7
C4—O2—C16117.4 (2)C10—C9—H9A108.7
C7—O3—C9108.10 (19)C8—C9—H9A108.7
C17—N1—C7112.8 (2)C11—C10—C15118.6 (3)
C17—N1—C8113.5 (2)C11—C10—C9120.3 (3)
C7—N1—C8102.6 (2)C15—C10—C9121.0 (2)
C6—C1—C2120.8 (3)C10—C11—C12120.7 (3)
C6—C1—H1A119.6C10—C11—H11A119.7
C2—C1—H1A119.6C12—C11—H11A119.7
C3—C2—C1119.7 (3)C13—C12—C11119.9 (3)
C3—C2—H2A120.1C13—C12—H12A120.0
C1—C2—H2A120.1C11—C12—H12A120.0
O1—C3—C2120.0 (3)C12—C13—C14120.0 (3)
O1—C3—C4120.0 (2)C12—C13—H13A120.0
C2—C3—C4119.9 (2)C14—C13—H13A120.0
O2—C4—C5125.7 (2)C15—C14—C13119.7 (3)
O2—C4—C3114.1 (2)C15—C14—H14A120.1
C5—C4—C3120.2 (2)C13—C14—H14A120.1
C4—C5—C6119.9 (3)C14—C15—C10121.0 (3)
C4—C5—H5A120.0C14—C15—H15A119.5
C6—C5—H5A120.0C10—C15—H15A119.5
C1—C6—C5119.4 (2)O2—C16—H16A109.5
C1—C6—C7120.8 (3)O2—C16—H16B109.5
C5—C6—C7119.8 (2)H16A—C16—H16B109.5
O3—C7—N1103.5 (2)O2—C16—H16C109.5
O3—C7—C6111.7 (2)H16A—C16—H16C109.5
N1—C7—C6112.8 (2)H16B—C16—H16C109.5
O3—C7—H7A109.5N1—C17—H17A109.5
N1—C7—H7A109.5N1—C17—H17C109.5
C6—C7—H7A109.5H17A—C17—H17C109.5
N1—C8—C18113.4 (2)N1—C17—H17D109.5
N1—C8—C9101.4 (2)H17A—C17—H17D109.5
C18—C8—C9113.2 (2)H17C—C17—H17D109.5
N1—C8—H8A109.5C8—C18—H18A109.5
C18—C8—H8A109.5C8—C18—H18D109.5
C9—C8—H8A109.5H18A—C18—H18D109.5
O3—C9—C10111.8 (2)C8—C18—H18B109.5
O3—C9—C8104.25 (19)H18A—C18—H18B109.5
C10—C9—C8114.5 (2)H18D—C18—H18B109.5
C6—C1—C2—C3−1.3 (4)C5—C6—C7—N1−69.3 (3)
C1—C2—C3—O1−179.5 (2)C17—N1—C8—C1873.7 (3)
C1—C2—C3—C4−0.4 (4)C7—N1—C8—C18−164.2 (2)
C16—O2—C4—C5−9.2 (4)C17—N1—C8—C9−164.6 (2)
C16—O2—C4—C3171.4 (2)C7—N1—C8—C9−42.5 (2)
O1—C3—C4—O20.7 (3)C7—O3—C9—C10−124.5 (2)
C2—C3—C4—O2−178.4 (2)C7—O3—C9—C8−0.3 (3)
O1—C3—C4—C5−178.7 (2)N1—C8—C9—O326.4 (2)
C2—C3—C4—C52.2 (4)C18—C8—C9—O3148.2 (2)
O2—C4—C5—C6178.4 (2)N1—C8—C9—C10148.9 (2)
C3—C4—C5—C6−2.3 (4)C18—C8—C9—C10−89.3 (3)
C2—C1—C6—C51.2 (4)O3—C9—C10—C11−136.8 (2)
C2—C1—C6—C7−174.8 (2)C8—C9—C10—C11104.9 (3)
C4—C5—C6—C10.6 (4)O3—C9—C10—C1545.9 (3)
C4—C5—C6—C7176.7 (2)C8—C9—C10—C15−72.4 (3)
C9—O3—C7—N1−26.2 (2)C15—C10—C11—C120.7 (4)
C9—O3—C7—C6−147.9 (2)C9—C10—C11—C12−176.7 (3)
C17—N1—C7—O3165.9 (2)C10—C11—C12—C130.5 (4)
C8—N1—C7—O343.3 (2)C11—C12—C13—C14−1.0 (5)
C17—N1—C7—C6−73.2 (3)C12—C13—C14—C150.3 (5)
C8—N1—C7—C6164.3 (2)C13—C14—C15—C100.9 (4)
C1—C6—C7—O3−137.2 (3)C11—C10—C15—C14−1.4 (4)
C5—C6—C7—O346.8 (3)C9—C10—C15—C14176.0 (3)
C1—C6—C7—N1106.7 (3)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 phenyl ring.
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O3i0.92 (4)2.08 (3)2.909 (3)148 (3)
C5—H5A···O1ii0.932.423.244 (3)148
C16—H16A···Cg1iii0.962.913.628 (3)133

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5455).

References

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