Literature DB >> 21580286

3-[(E)-1-(Benzyl-oxyimino)eth-yl]-2-oxo-2H-chromen-7-yl acetate.

Hui Wang1, Su-Hua Xu, Zhuo Zeng, Yong-Hong Zhang.   

Abstract

The title compound, C(20)H(17)NO(5), was prepared by the reaction of 3-acetyl-2-oxo-2H-chromen-7-yl acetate with benzyl-oxy-amine. The mol-ecule adopts an E configuration with respect to the C=N double bond. The dihedral angles between the coumarin ring system, the phenyl ring and the C=N-O-C plane of the oxime unit are 35.83 (6), 35.8 (2) and 69.99 (15)°, respectively. In the crystal, a two-dimensional supra-molecular network is assembled through weak inter-molecular C-H⋯O hydrogen-bonding inter-actions.

Entities:  

Year:  2010        PMID： 21580286      PMCID： PMC2983746          DOI： 10.1107/S1600536810003454

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


Related literature

For the pharmacological applications of Schiff base compounds derived from coumarins, see: Jolanta et al. (2006 ▶); Kontogiorgis et al. (2006 ▶); Kontogiorgis & Hadjipavlou-Litina (2004 ▶); Nofal et al. (2000 ▶). For their use as dyes, fluorescent agents and as chemosensors, see: Kachkovski et al. (2004 ▶); Turki et al. (2006 ▶); Li et al. (2009 ▶).

Experimental

Crystal data

C20H17NO5 M = 351.35 Triclinic, a = 6.3901 (9) Å b = 11.2413 (16) Å c = 12.9298 (18) Å α = 102.643 (2)° β = 96.923 (2)° γ = 101.860 (2)° V = 873.5 (2) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 298 K 0.25 × 0.20 × 0.18 mm

Data collection

Bruker APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.977, T max = 0.983 5311 measured reflections 3792 independent reflections 2335 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.166 S = 1.09 3792 reflections 238 parameters H-atom parameters constrained Δρmax = 0.33 e Å−3 Δρmin = −0.23 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003454/sj2717sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003454/sj2717Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H17NO5Z = 2
Mr = 351.35F(000) = 368
Triclinic, P1Dx = 1.336 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3901 (9) ÅCell parameters from 1332 reflections
b = 11.2413 (16) Åθ = 2.8–24.5°
c = 12.9298 (18) ŵ = 0.10 mm−1
α = 102.643 (2)°T = 298 K
β = 96.923 (2)°Block, colorless
γ = 101.860 (2)°0.25 × 0.20 × 0.18 mm
V = 873.5 (2) Å3
Bruker APEXII area-detector diffractometer3792 independent reflections
Radiation source: fine-focus sealed tube2335 reflections with I > 2σ(I)
graphiteRint = 0.025
φ and ω scansθmax = 27.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −8→6
Tmin = 0.977, Tmax = 0.983k = −12→14
5311 measured reflectionsl = −16→16
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.166w = 1/[σ2(Fo2) + (0.076P)2 + 0.0611P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
3792 reflectionsΔρmax = 0.33 e Å−3
238 parametersΔρmin = −0.23 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (4)
Experimental. FT—IR (KBr): 1763, 1717, 1615, 1426, 1365, 1200, 1030 cm-1; 1H NMR δ (400 Hz, DMSO, TMS): 8.08 (s, 1H), 7.83 (d, J = 8.4 Hz, 1H), 7.36–7.28 (m, 5H) 7.26 (d, J = 2.0 Hz, 1H), 7.14 (dd, J = 2.0, 8.4 Hz, 1H), 5.17 (s, 2H), 2.27 (s, 3H), 2.11 (s, 3H).
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
O1−0.33761 (19)0.48915 (12)0.62680 (10)0.0488 (4)
C2−0.2517 (3)0.56481 (18)0.72817 (15)0.0499 (5)
O2−0.3700 (2)0.62098 (15)0.77276 (12)0.0710 (5)
C3−0.0274 (3)0.56859 (17)0.77165 (15)0.0472 (5)
C40.0814 (3)0.49479 (17)0.71383 (15)0.0478 (5)
H40.22340.49700.74210.057*
C50.0893 (3)0.33485 (18)0.54693 (16)0.0504 (5)
H50.23010.33200.57250.060*
C6−0.0133 (3)0.26229 (17)0.44758 (16)0.0503 (5)
H60.05680.20970.40620.060*
C7−0.2229 (3)0.26729 (17)0.40849 (15)0.0448 (4)
O4−0.3080 (2)0.19654 (12)0.30368 (10)0.0542 (4)
C20−0.5180 (4)0.12835 (19)0.27716 (18)0.0591 (6)
O5−0.6377 (3)0.12328 (15)0.34060 (14)0.0791 (5)
C21−0.5679 (4)0.0639 (2)0.1608 (2)0.0821 (8)
H21C−0.71670.01730.14240.123*
H21A−0.47490.00760.14550.123*
H21B−0.54450.12510.11940.123*
C8−0.3309 (3)0.34359 (17)0.46779 (14)0.0450 (4)
H8−0.47060.34710.44100.054*
C9−0.2257 (3)0.41476 (16)0.56822 (14)0.0415 (4)
C10−0.0149 (3)0.41373 (16)0.61081 (14)0.0427 (4)
C110.0738 (3)0.65509 (19)0.87771 (16)0.0539 (5)
C120.0328 (4)0.7832 (2)0.90913 (19)0.0729 (7)
H12C0.16070.84040.95360.109*
H12B−0.08570.78040.94840.109*
H12A−0.00300.81110.84560.109*
N10.2041 (3)0.61121 (16)0.93402 (13)0.0644 (5)
O30.3083 (3)0.70165 (14)1.03000 (11)0.0744 (5)
C130.4579 (5)0.6475 (3)1.0870 (2)0.0940 (9)
H13B0.56900.62951.04520.113*
H13A0.38160.57001.10060.113*
C140.5568 (4)0.74251 (19)1.19015 (17)0.0609 (6)
C150.4399 (4)0.7731 (2)1.26843 (19)0.0677 (6)
H150.29370.73261.25730.081*
C160.5268 (5)0.8596 (2)1.3618 (2)0.0812 (8)
H160.44150.87721.41390.097*
C170.7365 (5)0.9205 (2)1.3795 (2)0.0820 (8)
H170.79440.98111.44370.098*
C180.8661 (4)0.8957 (3)1.3058 (2)0.0842 (8)
H181.01150.93841.31940.101*
C190.7778 (4)0.8050 (3)1.2092 (2)0.0817 (7)
H190.86440.78621.15790.098*
U11U22U33U12U13U23
O10.0384 (7)0.0550 (8)0.0484 (8)0.0149 (6)0.0013 (6)0.0035 (6)
C20.0446 (11)0.0558 (11)0.0473 (11)0.0116 (9)0.0061 (9)0.0102 (9)
O20.0508 (9)0.0869 (11)0.0646 (10)0.0236 (8)0.0070 (7)−0.0079 (8)
C30.0426 (10)0.0514 (11)0.0448 (10)0.0066 (8)0.0044 (8)0.0123 (8)
C40.0359 (10)0.0543 (11)0.0510 (11)0.0074 (8)0.0004 (8)0.0153 (9)
C50.0354 (10)0.0531 (11)0.0627 (12)0.0126 (8)0.0064 (9)0.0138 (9)
C60.0430 (11)0.0463 (10)0.0618 (12)0.0125 (8)0.0130 (9)0.0103 (9)
C70.0427 (10)0.0419 (9)0.0480 (11)0.0059 (8)0.0076 (8)0.0118 (8)
O40.0472 (8)0.0580 (8)0.0494 (8)0.0078 (6)0.0067 (6)0.0023 (6)
C200.0505 (13)0.0480 (11)0.0688 (14)0.0118 (9)0.0011 (11)−0.0009 (10)
O50.0550 (10)0.0705 (10)0.0932 (12)−0.0003 (8)0.0205 (9)−0.0079 (9)
C210.0753 (16)0.0762 (16)0.0731 (16)0.0155 (13)−0.0072 (13)−0.0128 (13)
C80.0374 (10)0.0488 (10)0.0481 (11)0.0125 (8)0.0029 (8)0.0109 (8)
C90.0377 (10)0.0428 (9)0.0464 (10)0.0126 (7)0.0081 (8)0.0128 (8)
C100.0364 (10)0.0432 (9)0.0472 (10)0.0058 (7)0.0054 (8)0.0134 (8)
C110.0495 (12)0.0610 (12)0.0456 (11)0.0079 (9)0.0042 (9)0.0091 (9)
C120.0735 (16)0.0703 (15)0.0628 (14)0.0169 (12)0.0027 (12)−0.0030 (11)
N10.0720 (12)0.0609 (11)0.0453 (10)0.0069 (9)−0.0095 (9)0.0015 (8)
O30.0890 (12)0.0662 (10)0.0523 (9)0.0159 (8)−0.0181 (8)0.0014 (7)
C130.126 (2)0.0769 (17)0.0661 (16)0.0340 (16)−0.0280 (15)0.0053 (13)
C140.0722 (15)0.0542 (12)0.0487 (12)0.0134 (11)−0.0092 (11)0.0092 (9)
C150.0686 (15)0.0641 (14)0.0688 (15)0.0136 (11)0.0064 (12)0.0186 (12)
C160.109 (2)0.0721 (16)0.0676 (16)0.0310 (16)0.0149 (15)0.0201 (13)
C170.099 (2)0.0624 (15)0.0700 (17)0.0142 (15)−0.0147 (16)0.0070 (13)
C180.0612 (16)0.0781 (17)0.098 (2)−0.0013 (13)−0.0165 (15)0.0231 (15)
C190.0776 (18)0.0987 (19)0.0770 (17)0.0287 (15)0.0165 (14)0.0307 (15)
O1—C91.372 (2)C9—C101.396 (2)
O1—C21.375 (2)C11—N11.283 (3)
C2—O21.202 (2)C11—C121.494 (3)
C2—C31.464 (3)C12—H12C0.9600
C3—C41.350 (3)C12—H12B0.9600
C3—C111.479 (3)C12—H12A0.9600
C4—C101.423 (2)N1—O31.410 (2)
C4—H40.9300O3—C131.447 (3)
C5—C61.365 (3)C13—C141.489 (3)
C5—C101.403 (3)C13—H13B0.9700
C5—H50.9300C13—H13A0.9700
C6—C71.390 (3)C14—C151.355 (3)
C6—H60.9300C14—C191.408 (3)
C7—C81.372 (3)C15—C161.347 (3)
C7—O41.392 (2)C15—H150.9300
O4—C201.363 (2)C16—C171.340 (4)
C20—O51.190 (2)C16—H160.9300
C20—C211.483 (3)C17—C181.356 (4)
C21—H21C0.9600C17—H170.9300
C21—H21A0.9600C18—C191.398 (4)
C21—H21B0.9600C18—H180.9300
C8—C91.375 (2)C19—H190.9300
C8—H80.9300
C9—O1—C2122.88 (14)C5—C10—C4124.61 (17)
O2—C2—O1116.29 (17)N1—C11—C3113.44 (18)
O2—C2—C3126.37 (18)N1—C11—C12125.35 (19)
O1—C2—C3117.34 (17)C3—C11—C12121.10 (18)
C4—C3—C2119.42 (17)C11—C12—H12C109.5
C4—C3—C11122.05 (18)C11—C12—H12B109.5
C2—C3—C11118.53 (17)H12C—C12—H12B109.5
C3—C4—C10121.90 (17)C11—C12—H12A109.5
C3—C4—H4119.0H12C—C12—H12A109.5
C10—C4—H4119.0H12B—C12—H12A109.5
C6—C5—C10120.80 (17)C11—N1—O3110.70 (17)
C6—C5—H5119.6N1—O3—C13107.54 (16)
C10—C5—H5119.6O3—C13—C14106.20 (19)
C5—C6—C7119.80 (18)O3—C13—H13B110.5
C5—C6—H6120.1C14—C13—H13B110.5
C7—C6—H6120.1O3—C13—H13A110.5
C8—C7—C6121.47 (17)C14—C13—H13A110.5
C8—C7—O4122.92 (16)H13B—C13—H13A108.7
C6—C7—O4115.48 (16)C15—C14—C19117.5 (2)
C20—O4—C7120.76 (15)C15—C14—C13122.1 (2)
O5—C20—O4123.2 (2)C19—C14—C13120.4 (2)
O5—C20—C21127.0 (2)C16—C15—C14122.7 (2)
O4—C20—C21109.8 (2)C16—C15—H15118.7
C20—C21—H21C109.5C14—C15—H15118.7
C20—C21—H21A109.5C17—C16—C15119.9 (3)
H21C—C21—H21A109.5C17—C16—H16120.0
C20—C21—H21B109.5C15—C16—H16120.0
H21C—C21—H21B109.5C16—C17—C18121.5 (3)
H21A—C21—H21B109.5C16—C17—H17119.3
C7—C8—C9117.84 (17)C18—C17—H17119.3
C7—C8—H8121.1C17—C18—C19119.0 (3)
C9—C8—H8121.1C17—C18—H18120.5
O1—C9—C8116.92 (15)C19—C18—H18120.5
O1—C9—C10120.20 (16)C18—C19—C14119.4 (2)
C8—C9—C10122.89 (16)C18—C19—H19120.3
C9—C10—C5117.19 (17)C14—C19—H19120.3
C9—C10—C4118.17 (16)
C9—O1—C2—O2−176.76 (17)C8—C9—C10—C4177.57 (16)
C9—O1—C2—C32.8 (3)C6—C5—C10—C9−0.2 (3)
O2—C2—C3—C4176.5 (2)C6—C5—C10—C4−178.29 (17)
O1—C2—C3—C4−3.0 (3)C3—C4—C10—C92.0 (3)
O2—C2—C3—C11−4.3 (3)C3—C4—C10—C5−179.96 (18)
O1—C2—C3—C11176.28 (16)C4—C3—C11—N1−36.2 (3)
C2—C3—C4—C100.6 (3)C2—C3—C11—N1144.62 (19)
C11—C3—C4—C10−178.60 (16)C4—C3—C11—C12140.3 (2)
C10—C5—C6—C70.7 (3)C2—C3—C11—C12−38.9 (3)
C5—C6—C7—C8−0.3 (3)C3—C11—N1—O3175.21 (16)
C5—C6—C7—O4175.76 (16)C12—C11—N1—O3−1.1 (3)
C8—C7—O4—C20−45.7 (2)C11—N1—O3—C13−177.84 (19)
C6—C7—O4—C20138.31 (18)N1—O3—C13—C14−177.2 (2)
C7—O4—C20—O5−1.4 (3)O3—C13—C14—C1567.9 (3)
C7—O4—C20—C21179.04 (17)O3—C13—C14—C19−111.6 (3)
C6—C7—C8—C9−0.6 (3)C19—C14—C15—C160.1 (3)
O4—C7—C8—C9−176.27 (15)C13—C14—C15—C16−179.4 (2)
C2—O1—C9—C8179.99 (16)C14—C15—C16—C170.8 (4)
C2—O1—C9—C10−0.1 (3)C15—C16—C17—C18−1.0 (4)
C7—C8—C9—O1−179.15 (15)C16—C17—C18—C190.4 (4)
C7—C8—C9—C101.0 (3)C17—C18—C19—C140.6 (4)
O1—C9—C10—C5179.54 (15)C15—C14—C19—C18−0.8 (3)
C8—C9—C10—C5−0.6 (3)C13—C14—C19—C18178.8 (2)
O1—C9—C10—C4−2.3 (2)
D—H···AD—HH···AD···AD—H···A
C6—H6···O5i0.932.513.393 (3)159
C18—H18···O5ii0.932.673.552 (3)160
C8—H8···O1iii0.932.653.397 (2)138
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C6—H6⋯O5i0.932.513.393 (3)159
C18—H18⋯O5ii0.932.673.552 (3)160
C8—H8⋯O1iii0.932.653.397 (2)138

Symmetry codes: (i) ; (ii) ; (iii) .

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