Literature DB >> 22589883

4-[(3-Meth-oxy-anilino)methyl-idene]-2-phenyl-1,3-oxazol-5(4H)-one.

Wan-Yun Huang, Ye Zhang, Kun Hu, Qing-Mei Lin, Xian-Xian Liu.   

Abstract

In the title compound, C(17)H(14)N(2)O(3), the n class="Chemical">oxazolone ring is essentially planar [maximum deviation = 0.004 (1) Å] and is oriented with respect to the phenyl and benzene rings at 10.06 (9) and 5.63 (8)°, respectively; the dihedral angle between the phenyl ring and the benzene ring is 15.69 (8)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains running along the a axis. Neighbouring chains are inter-connected by π-π stacking, the centroid-centroid distance being 3.6201 (9) Å.

Entities:  

Year:  2012        PMID： 22589883      PMCID： PMC3343974          DOI： 10.1107/S1600536812008276

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to the oxazolones, see: Fisk et al. (2007 ▶); Mosey et al. (2008 ▶); Hewlett et al. (2009 ▶). For the bioactivities of 4-(amino­methyl­ene)-2-phenyl-4H-oxazol-5-one derivatives, see: Tandon et al. (2004 ▶); John et al. (2008 ▶). For the synthesis, see: Matos et al. (2003 ▶). For related structures, see: Romeiro et al. (2010 ▶); Vasuki et al. (2002 ▶).

Experimental

Crystal data

C17H14N2O3 M = 294.30 Triclinic, a = 6.6085 (5) Å b = 7.1887 (5) Å c = 15.3659 (10) Å α = 98.629 (5)° β = 94.096 (5)° γ = 108.715 (6)° V = 677.96 (8) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 150 K 0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova (single source at offset) Eos diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.975, T max = 0.985 5557 measured reflections 2759 independent reflections 2317 reflections with I > 2σ(I) R int = 0.023 Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.118 S = 1.02 2759 reflections 204 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.22 e Å−3 Δρmin = −0.29 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOn class="Chemical">ND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008276/xu5464sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008276/xu5464Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812008276/xu5464Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H14N2O3Z = 2
Mr = 294.30F(000) = 308
Triclinic, P1Dx = 1.442 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6085 (5) ÅCell parameters from 2524 reflections
b = 7.1887 (5) Åθ = 3.0–28.7°
c = 15.3659 (10) ŵ = 0.10 mm−1
α = 98.629 (5)°T = 150 K
β = 94.096 (5)°Block, green
γ = 108.715 (6)°0.25 × 0.20 × 0.15 mm
V = 677.96 (8) Å3
Agilent SuperNova (single source at offset) Eos diffractometer2759 independent reflections
Radiation source: fine-focus sealed tube2317 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)h = −8→8
Tmin = 0.975, Tmax = 0.985k = −8→8
5557 measured reflectionsl = −19→19
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) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.060P)2 + 0.1704P] where P = (Fo2 + 2Fc2)/3
2759 reflections(Δ/σ)max < 0.001
204 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Experimental. 1H NMR (DMSO, 500 MHz) δ: 10.70 (d, 1H, NH), 7.97–8.05 (m, 3H, Ar—H), 7.55–7.57(m, 3H, Ar—H), 7.25 (t, 1H, Ar—H), 7.10–7.14 (m, 2H, Ar—H), 6.67 (q, 1H, Ar—H), 3.78 (s, 3H, CH3). 13C NMR (DMSO, 125.77 MHz) δ: 167.11, 160.27, 154.44, 141.21, 135.31, 131.34, 130.28, 129.09, 126.55, 126.40, 125.82, 111.06, 109.81, 109.29, 102.70, 55.23.
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.
xyzUiso*/Ueq
C10.2537 (3)0.6133 (3)0.85604 (11)0.0242 (4)
H10.33960.57320.81510.029*
C20.3478 (3)0.7213 (3)0.93963 (11)0.0311 (4)
H20.49810.75440.95620.037*
C30.2225 (3)0.7811 (3)0.99922 (11)0.0318 (4)
H30.28760.85521.05650.038*
C40.0043 (3)0.7337 (3)0.97570 (11)0.0297 (4)
H4−0.08030.77621.01650.036*
C5−0.0917 (3)0.6238 (3)0.89242 (11)0.0243 (4)
H5−0.24250.58950.87660.029*
C60.0327 (2)0.5636 (2)0.83184 (10)0.0189 (3)
C7−0.0642 (2)0.4518 (2)0.74310 (10)0.0176 (3)
C8−0.3384 (3)0.2824 (2)0.63810 (10)0.0192 (3)
C9−0.1337 (2)0.3036 (2)0.60730 (10)0.0177 (3)
C10−0.1006 (2)0.2327 (2)0.52347 (10)0.0177 (3)
H10−0.22160.16600.47960.021*
C110.1565 (3)0.2043 (2)0.41664 (9)0.0179 (3)
C120.3751 (3)0.2674 (2)0.40875 (10)0.0194 (3)
H120.47740.34090.45880.023*
C130.4433 (3)0.2222 (2)0.32722 (10)0.0214 (4)
H130.59250.26690.32130.026*
C140.2950 (3)0.1127 (2)0.25468 (10)0.0220 (4)
H140.34220.08180.19910.026*
C150.0758 (3)0.0477 (2)0.26330 (10)0.0184 (3)
C160.0038 (2)0.0943 (2)0.34428 (10)0.0184 (3)
H16−0.14570.05220.34990.022*
C17−0.2821 (3)−0.1308 (3)0.19348 (11)0.0292 (4)
H17A−0.3122−0.21170.24000.044*
H17B−0.3592−0.21180.13640.044*
H17C−0.3300−0.01540.20770.044*
N10.0328 (2)0.41031 (19)0.67659 (8)0.0183 (3)
N20.0970 (2)0.2548 (2)0.50167 (9)0.0194 (3)
O1−0.52599 (17)0.20389 (18)0.60520 (7)0.0254 (3)
O2−0.28635 (16)0.38163 (16)0.72695 (7)0.0195 (3)
O3−0.05667 (17)−0.06328 (17)0.18811 (7)0.0235 (3)
H2A0.211 (3)0.304 (3)0.5461 (13)0.036 (5)*
U11U22U33U12U13U23
C10.0235 (9)0.0242 (9)0.0223 (8)0.0044 (7)0.0045 (7)0.0031 (7)
C20.0262 (9)0.0315 (10)0.0271 (9)0.0013 (8)−0.0029 (7)0.0013 (8)
C30.0432 (11)0.0260 (10)0.0179 (8)0.0048 (8)−0.0032 (8)−0.0026 (7)
C40.0415 (11)0.0292 (10)0.0195 (8)0.0148 (8)0.0068 (8)0.0006 (7)
C50.0278 (9)0.0256 (9)0.0211 (8)0.0117 (7)0.0037 (7)0.0033 (7)
C60.0229 (8)0.0160 (8)0.0172 (8)0.0054 (6)0.0026 (6)0.0043 (6)
C70.0183 (8)0.0166 (8)0.0189 (8)0.0063 (6)0.0037 (6)0.0046 (6)
C80.0226 (9)0.0213 (8)0.0153 (7)0.0096 (7)0.0034 (6)0.0030 (6)
C90.0182 (8)0.0186 (8)0.0167 (7)0.0066 (6)0.0029 (6)0.0034 (6)
C100.0190 (8)0.0176 (8)0.0174 (7)0.0074 (6)0.0016 (6)0.0031 (6)
C110.0244 (8)0.0161 (8)0.0161 (8)0.0098 (6)0.0053 (6)0.0038 (6)
C120.0200 (8)0.0185 (8)0.0188 (8)0.0061 (6)0.0022 (6)0.0018 (6)
C130.0199 (8)0.0222 (9)0.0233 (8)0.0076 (7)0.0070 (7)0.0047 (7)
C140.0247 (9)0.0258 (9)0.0178 (8)0.0106 (7)0.0086 (7)0.0035 (7)
C150.0225 (8)0.0172 (8)0.0163 (7)0.0075 (6)0.0022 (6)0.0034 (6)
C160.0176 (8)0.0200 (8)0.0201 (8)0.0085 (6)0.0056 (6)0.0052 (6)
C170.0196 (9)0.0384 (11)0.0251 (9)0.0087 (8)0.0001 (7)−0.0043 (7)
N10.0184 (7)0.0196 (7)0.0170 (6)0.0064 (5)0.0037 (5)0.0028 (5)
N20.0170 (7)0.0246 (8)0.0156 (7)0.0073 (6)0.0025 (5)0.0001 (5)
O10.0177 (6)0.0362 (7)0.0209 (6)0.0083 (5)0.0005 (5)0.0030 (5)
O20.0157 (6)0.0264 (6)0.0151 (5)0.0068 (5)0.0031 (4)−0.0003 (4)
O30.0217 (6)0.0296 (7)0.0158 (6)0.0059 (5)0.0027 (5)−0.0002 (5)
C1—C21.384 (2)C10—N21.337 (2)
C1—C61.395 (2)C10—H100.9500
C1—H10.9500C11—C121.389 (2)
C2—C31.388 (3)C11—C161.394 (2)
C2—H20.9500C11—N21.4201 (19)
C3—C41.378 (3)C12—C131.389 (2)
C3—H30.9500C12—H120.9500
C4—C51.387 (2)C13—C141.381 (2)
C4—H40.9500C13—H130.9500
C5—C61.396 (2)C14—C151.395 (2)
C5—H50.9500C14—H140.9500
C6—C71.460 (2)C15—O31.3670 (19)
C7—N11.2917 (19)C15—C161.396 (2)
C7—O21.3810 (18)C16—H160.9500
C8—O11.2191 (19)C17—O31.4237 (19)
C8—O21.4051 (18)C17—H17A0.9800
C8—C91.435 (2)C17—H17B0.9800
C9—C101.372 (2)C17—H17C0.9800
C9—N11.407 (2)N2—H2A0.92 (2)
C2—C1—C6120.00 (16)C12—C11—C16121.14 (14)
C2—C1—H1120.0C12—C11—N2116.95 (14)
C6—C1—H1120.0C16—C11—N2121.90 (14)
C1—C2—C3120.03 (17)C13—C12—C11119.60 (15)
C1—C2—H2120.0C13—C12—H12120.2
C3—C2—H2120.0C11—C12—H12120.2
C4—C3—C2120.38 (16)C14—C13—C12120.30 (15)
C4—C3—H3119.8C14—C13—H13119.8
C2—C3—H3119.8C12—C13—H13119.8
C3—C4—C5120.01 (16)C13—C14—C15119.82 (14)
C3—C4—H4120.0C13—C14—H14120.1
C5—C4—H4120.0C15—C14—H14120.1
C4—C5—C6120.10 (16)O3—C15—C14115.12 (13)
C4—C5—H5119.9O3—C15—C16124.11 (14)
C6—C5—H5119.9C14—C15—C16120.77 (15)
C1—C6—C5119.48 (15)C11—C16—C15118.35 (14)
C1—C6—C7119.49 (14)C11—C16—H16120.8
C5—C6—C7121.03 (15)C15—C16—H16120.8
N1—C7—O2115.14 (13)O3—C17—H17A109.5
N1—C7—C6127.89 (14)O3—C17—H17B109.5
O2—C7—C6116.97 (13)H17A—C17—H17B109.5
O1—C8—O2120.54 (14)O3—C17—H17C109.5
O1—C8—C9135.12 (15)H17A—C17—H17C109.5
O2—C8—C9104.33 (13)H17B—C17—H17C109.5
C10—C9—N1124.09 (14)C7—N1—C9104.91 (13)
C10—C9—C8126.24 (15)C10—N2—C11128.04 (14)
N1—C9—C8109.67 (13)C10—N2—H2A118.3 (12)
N2—C10—C9121.89 (15)C11—N2—H2A113.6 (13)
N2—C10—H10119.1C7—O2—C8105.95 (11)
C9—C10—H10119.1C15—O3—C17117.09 (12)
C6—C1—C2—C3−0.4 (3)C12—C13—C14—C150.2 (2)
C1—C2—C3—C40.0 (3)C13—C14—C15—O3−178.56 (13)
C2—C3—C4—C50.6 (3)C13—C14—C15—C160.9 (2)
C3—C4—C5—C6−0.9 (3)C12—C11—C16—C150.4 (2)
C2—C1—C6—C50.1 (2)N2—C11—C16—C15−178.82 (13)
C2—C1—C6—C7179.27 (15)O3—C15—C16—C11178.24 (13)
C4—C5—C6—C10.5 (2)C14—C15—C16—C11−1.2 (2)
C4—C5—C6—C7−178.59 (14)O2—C7—N1—C90.53 (17)
C1—C6—C7—N1−9.5 (2)C6—C7—N1—C9−179.07 (14)
C5—C6—C7—N1169.59 (15)C10—C9—N1—C7179.11 (14)
C1—C6—C7—O2170.88 (13)C8—C9—N1—C7−0.69 (16)
C5—C6—C7—O2−10.0 (2)C9—C10—N2—C11−174.39 (14)
O1—C8—C9—C100.7 (3)C12—C11—N2—C10171.24 (15)
O2—C8—C9—C10−179.20 (14)C16—C11—N2—C10−9.5 (2)
O1—C8—C9—N1−179.47 (17)N1—C7—O2—C8−0.17 (17)
O2—C8—C9—N10.59 (16)C6—C7—O2—C8179.48 (12)
N1—C9—C10—N22.3 (2)O1—C8—O2—C7179.78 (14)
C8—C9—C10—N2−177.99 (14)C9—C8—O2—C7−0.27 (15)
C16—C11—C12—C130.7 (2)C14—C15—O3—C17−179.23 (14)
N2—C11—C12—C13179.92 (14)C16—C15—O3—C171.3 (2)
C11—C12—C13—C14−1.0 (2)
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.92 (2)2.26 (2)3.0110 (18)138.1 (17)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2A⋯O1i0.92 (2)2.26 (2)3.0110 (18)138.1 (17)

Symmetry code: (i) .

  4 in total

Review 1.  The diverse chemistry of oxazol-5-(4H)-ones.

Authors:  Jason S Fisk; Robert A Mosey; Jetze J Tepe
Journal:  Chem Soc Rev       Date:  2007-03-12       Impact factor: 54.564

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  4-[(Dimethyl-amino)methyl-idene]-2-(4-nitro-phen-yl)-1,3-oxazol-5(4H)-one.

Authors:  Gilberto A Romeiro; Carlos M R Ribeiro; Solange M S V Wardell; James L Wardell; Seik Weng Ng; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-26

4.  Potent and selective inhibitors of bacterial methionyl tRNA synthetase derived from an oxazolone-dipeptide scaffold.

Authors:  Manish Tandon; David L Coffen; Paul Gallant; Dennis Keith; Mark A Ashwell
Journal:  Bioorg Med Chem Lett       Date:  2004-04-19       Impact factor: 2.823
  4 in total
  1 in total

1.  Crystal structure of 2-methyl-4-[(thio-phen-2-yl)methyl-idene]-1,3-oxazol-5(4H)-one.

Authors:  Preetika Sharma; K N Subbulakshmi; B Narayana; K Byrappa; Rajni Kant
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-21
  1 in total

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