Literature DB >> 21581291

Ethyl 2-[4-(benzyloxy)anilino]-4-oxo-4,5-dihydro-furan-3-carboxyl-ate.

S Nirmala, R Murugan, E Theboral Sugi Kamala, L Sudha, S Sriman Narayanan.   

Abstract

In the title compound, C(20)H(19)NO(5), the dihydro-furan ring is almost planar [maximum deviation of 0.021 (2)°] and makes dihedral angles of 28.1 (7) and 54.5 (5)° with the benzyl and phenyl-amino rings, respectively. The mol-ecular packing is stabilized by intra-molecular N-H⋯O hydrogen bonds and inter-molecular C-H⋯O inter-actions.

Entities:  

Year:  2008        PMID： 21581291      PMCID： PMC2960036          DOI： 10.1107/S1600536808035988

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


Related literature

For background on the development of effective and tolerable therapeutic options for cervical cancer, see: Huang et al. (2007 ▶); Lu et al. (2008 ▶). For the analysis of apoptosis induced by dihydro­furan carboxyl­ate compounds, see: Chen et al. (2006 ▶); Lin et al. (2006 ▶); Zhang & Wei (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Erdsack et al. (2007 ▶).

Experimental

Crystal data

C20H19NO5 M = 353.36 Triclinic, a = 9.1315 (3) Å b = 10.4040 (3) Å c = 11.1162 (4) Å α = 84.848 (2)° β = 66.436 (2)° γ = 64.121 (2)° V = 866.34 (5) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 293 (2) K 0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.976, T max = 0.981 22596 measured reflections 5349 independent reflections 3665 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.163 S = 1.03 5349 reflections 235 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.20 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035988/bq2103sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035988/bq2103Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H19NO5Z = 2
Mr = 353.36F000 = 372
Triclinic, P1Dx = 1.355 Mg m−3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.1315 (3) ÅCell parameters from 6361 reflections
b = 10.4040 (3) Åθ = 2.6–30.7º
c = 11.1162 (4) ŵ = 0.10 mm−1
α = 84.848 (2)ºT = 293 (2) K
β = 66.436 (2)ºPrism, yellow
γ = 64.121 (2)º0.25 × 0.20 × 0.20 mm
V = 866.34 (5) Å3
Bruker Kappa APEXII diffractometer5349 independent reflections
Radiation source: fine-focus sealed tube3665 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 293(2) Kθmax = 30.7º
Bruker axs (kappa apex2) scansθmin = 2.0º
Absorption correction: multi-scan(Blessing, 1995)h = −13→13
Tmin = 0.976, Tmax = 0.981k = −14→14
22596 measured reflectionsl = −15→15
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) = 0.163  w = 1/[σ2(Fo2) + (0.0812P)2 + 0.1488P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5349 reflectionsΔρmax = 0.29 e Å−3
235 parametersΔρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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
C11.26357 (19)0.57501 (15)0.0775 (2)0.0570 (4)
H1A1.32520.57140.13230.068*
H1B1.32240.6003−0.00860.068*
C21.26228 (18)0.43137 (14)0.06491 (15)0.0437 (3)
C31.07887 (17)0.46034 (12)0.12356 (14)0.0386 (3)
C40.98080 (17)0.60818 (13)0.15886 (14)0.0396 (3)
C50.71086 (17)0.83503 (13)0.24252 (14)0.0421 (3)
C60.58376 (19)0.91391 (14)0.19371 (16)0.0496 (3)
H60.56280.86840.13830.060*
C70.4878 (2)1.06059 (15)0.22738 (17)0.0517 (4)
H70.40111.11380.19560.062*
C80.52074 (18)1.12851 (14)0.30861 (15)0.0447 (3)
C90.6476 (2)1.04905 (15)0.35756 (16)0.0515 (4)
H90.66991.09410.41220.062*
C100.7412 (2)0.90186 (15)0.32472 (16)0.0513 (4)
H100.82530.84790.35870.062*
C110.4551 (2)1.34824 (16)0.41338 (19)0.0572 (4)
H11A0.57621.33710.36980.069*
H11B0.43961.31040.49830.069*
C120.3260 (2)1.50396 (14)0.43163 (15)0.0464 (3)
C130.1520 (2)1.54983 (19)0.51716 (18)0.0639 (4)
H130.11361.48360.56350.077*
C140.0329 (3)1.6920 (2)0.5359 (2)0.0798 (6)
H14−0.08531.72160.59400.096*
C150.0884 (3)1.78924 (19)0.4692 (3)0.0816 (7)
H150.00831.88580.48180.098*
C160.2604 (4)1.7455 (2)0.3842 (3)0.0888 (7)
H160.29831.81240.33900.107*
C170.3794 (3)1.6028 (2)0.3642 (2)0.0678 (5)
H170.49681.57340.30450.081*
C180.99189 (18)0.36906 (13)0.14162 (14)0.0416 (3)
C191.0226 (3)0.13250 (17)0.1330 (3)0.0729 (6)
H19A0.92520.15710.21930.088*
H19B0.97550.14090.06690.088*
C201.1542 (3)−0.01258 (19)0.1230 (3)0.0969 (8)
H20A1.1010−0.07720.13620.145*
H20B1.1996−0.02050.18920.145*
H20C1.2498−0.03670.03720.145*
N10.80732 (15)0.68332 (11)0.20754 (13)0.0465 (3)
H10.74560.63660.21960.056*
O10.42051 (15)1.27356 (10)0.33465 (12)0.0582 (3)
O21.07889 (13)0.67841 (9)0.13778 (12)0.0516 (3)
O31.39676 (13)0.32190 (11)0.01100 (13)0.0599 (3)
O40.83217 (13)0.41370 (11)0.18030 (13)0.0568 (3)
O51.10361 (13)0.22984 (10)0.11310 (12)0.0522 (3)
U11U22U33U12U13U23
C10.0359 (7)0.0384 (7)0.0945 (12)−0.0144 (6)−0.0230 (7)−0.0096 (7)
C20.0369 (6)0.0328 (6)0.0618 (8)−0.0125 (5)−0.0221 (6)−0.0017 (5)
C30.0350 (6)0.0269 (5)0.0514 (7)−0.0118 (4)−0.0164 (5)0.0010 (5)
C40.0365 (6)0.0293 (5)0.0512 (7)−0.0138 (5)−0.0161 (5)0.0010 (5)
C50.0329 (6)0.0283 (5)0.0550 (8)−0.0099 (5)−0.0111 (5)−0.0017 (5)
C60.0440 (7)0.0350 (6)0.0669 (9)−0.0108 (6)−0.0241 (7)−0.0080 (6)
C70.0477 (8)0.0345 (6)0.0683 (10)−0.0062 (6)−0.0297 (7)−0.0062 (6)
C80.0396 (7)0.0313 (6)0.0531 (8)−0.0074 (5)−0.0159 (6)−0.0064 (5)
C90.0499 (8)0.0383 (7)0.0627 (9)−0.0108 (6)−0.0261 (7)−0.0081 (6)
C100.0473 (8)0.0365 (7)0.0638 (9)−0.0073 (6)−0.0275 (7)−0.0013 (6)
C110.0551 (9)0.0374 (7)0.0748 (11)−0.0102 (6)−0.0299 (8)−0.0108 (7)
C120.0490 (8)0.0342 (6)0.0518 (8)−0.0126 (6)−0.0204 (6)−0.0068 (5)
C130.0594 (10)0.0494 (9)0.0610 (10)−0.0147 (8)−0.0135 (8)0.0040 (7)
C140.0601 (11)0.0616 (11)0.0776 (13)0.0030 (9)−0.0178 (10)−0.0184 (10)
C150.0951 (16)0.0345 (8)0.1246 (18)−0.0077 (9)−0.0732 (15)−0.0061 (10)
C160.1034 (18)0.0548 (11)0.144 (2)−0.0476 (12)−0.0750 (17)0.0374 (12)
C170.0592 (10)0.0604 (10)0.0887 (13)−0.0320 (9)−0.0288 (10)0.0112 (9)
C180.0398 (7)0.0289 (5)0.0547 (8)−0.0148 (5)−0.0179 (6)0.0041 (5)
C190.0681 (11)0.0381 (8)0.1251 (17)−0.0328 (8)−0.0411 (11)0.0130 (9)
C200.0866 (15)0.0382 (9)0.163 (3)−0.0326 (10)−0.0444 (16)0.0207 (12)
N10.0357 (6)0.0280 (5)0.0686 (8)−0.0124 (4)−0.0146 (5)−0.0015 (5)
O10.0597 (7)0.0308 (5)0.0779 (8)−0.0033 (4)−0.0362 (6)−0.0140 (5)
O20.0383 (5)0.0299 (4)0.0823 (8)−0.0144 (4)−0.0185 (5)−0.0058 (4)
O30.0359 (5)0.0388 (5)0.0931 (9)−0.0083 (4)−0.0198 (5)−0.0128 (5)
O40.0388 (5)0.0388 (5)0.0878 (8)−0.0184 (4)−0.0185 (5)0.0037 (5)
O50.0450 (5)0.0266 (4)0.0821 (8)−0.0160 (4)−0.0215 (5)0.0018 (4)
C1—O21.4466 (17)C11—H11A0.9700
C1—C21.5190 (19)C11—H11B0.9700
C1—H1A0.9700C12—C171.365 (2)
C1—H1B0.9700C12—C131.367 (2)
C2—O31.2156 (16)C13—C141.373 (2)
C2—C31.4291 (19)C13—H130.9300
C3—C41.3953 (16)C14—C151.357 (3)
C3—C181.4386 (17)C14—H140.9300
C4—N11.3126 (17)C15—C161.354 (4)
C4—O21.3281 (15)C15—H150.9300
C5—C101.371 (2)C16—C171.376 (3)
C5—C61.381 (2)C16—H160.9300
C5—N11.4287 (15)C17—H170.9300
C6—C71.3820 (18)C18—O41.2128 (17)
C6—H60.9300C18—O51.3316 (15)
C7—C81.387 (2)C19—C201.441 (3)
C7—H70.9300C19—O51.4506 (17)
C8—O11.3637 (15)C19—H19A0.9700
C8—C91.381 (2)C19—H19B0.9700
C9—C101.3847 (19)C20—H20A0.9600
C9—H90.9300C20—H20B0.9600
C10—H100.9300C20—H20C0.9600
C11—O11.4238 (18)N1—H10.8600
C11—C121.5022 (19)
O2—C1—C2105.83 (11)C17—C12—C13118.54 (15)
O2—C1—H1A110.6C17—C12—C11121.00 (15)
C2—C1—H1A110.6C13—C12—C11120.46 (15)
O2—C1—H1B110.6C12—C13—C14121.09 (18)
C2—C1—H1B110.6C12—C13—H13119.5
H1A—C1—H1B108.7C14—C13—H13119.5
O3—C2—C3131.81 (12)C15—C14—C13119.7 (2)
O3—C2—C1122.98 (13)C15—C14—H14120.1
C3—C2—C1105.18 (11)C13—C14—H14120.1
C4—C3—C2106.96 (11)C16—C15—C14119.92 (17)
C4—C3—C18121.03 (12)C16—C15—H15120.0
C2—C3—C18131.90 (11)C14—C15—H15120.0
N1—C4—O2117.79 (11)C15—C16—C17120.4 (2)
N1—C4—C3127.88 (12)C15—C16—H16119.8
O2—C4—C3114.33 (11)C17—C16—H16119.8
C10—C5—C6120.12 (12)C12—C17—C16120.32 (19)
C10—C5—N1120.95 (13)C12—C17—H17119.8
C6—C5—N1118.92 (13)C16—C17—H17119.8
C5—C6—C7119.82 (13)O4—C18—O5122.88 (12)
C5—C6—H6120.1O4—C18—C3123.59 (12)
C7—C6—H6120.1O5—C18—C3113.52 (11)
C6—C7—C8120.03 (14)C20—C19—O5109.29 (15)
C6—C7—H7120.0C20—C19—H19A109.8
C8—C7—H7120.0O5—C19—H19A109.8
O1—C8—C9124.60 (13)C20—C19—H19B109.8
O1—C8—C7115.48 (13)O5—C19—H19B109.8
C9—C8—C7119.92 (12)H19A—C19—H19B108.3
C8—C9—C10119.57 (14)C19—C20—H20A109.5
C8—C9—H9120.2C19—C20—H20B109.5
C10—C9—H9120.2H20A—C20—H20B109.5
C5—C10—C9120.52 (14)C19—C20—H20C109.5
C5—C10—H10119.7H20A—C20—H20C109.5
C9—C10—H10119.7H20B—C20—H20C109.5
O1—C11—C12107.46 (12)C4—N1—C5126.48 (11)
O1—C11—H11A110.2C4—N1—H1116.8
C12—C11—H11A110.2C5—N1—H1116.8
O1—C11—H11B110.2C8—O1—C11117.26 (12)
C12—C11—H11B110.2C4—O2—C1107.56 (10)
H11A—C11—H11B108.5C18—O5—C19115.87 (12)
O2—C1—C2—O3175.75 (15)C12—C13—C14—C15−0.4 (3)
O2—C1—C2—C3−2.44 (18)C13—C14—C15—C160.3 (3)
O3—C2—C3—C4−174.22 (17)C14—C15—C16—C170.4 (4)
C1—C2—C3—C43.74 (17)C13—C12—C17—C161.0 (3)
O3—C2—C3—C181.9 (3)C11—C12—C17—C16−178.56 (18)
C1—C2—C3—C18179.84 (16)C15—C16—C17—C12−1.1 (3)
C2—C3—C4—N1174.99 (15)C4—C3—C18—O44.4 (2)
C18—C3—C4—N1−1.6 (2)C2—C3—C18—O4−171.19 (16)
C2—C3—C4—O2−4.03 (17)C4—C3—C18—O5−174.86 (13)
C18—C3—C4—O2179.36 (13)C2—C3—C18—O59.5 (2)
C10—C5—C6—C70.3 (2)O2—C4—N1—C5−0.9 (2)
N1—C5—C6—C7179.38 (14)C3—C4—N1—C5−179.88 (14)
C5—C6—C7—C80.8 (2)C10—C5—N1—C4−52.3 (2)
C6—C7—C8—O1179.24 (15)C6—C5—N1—C4128.62 (17)
C6—C7—C8—C9−1.1 (2)C9—C8—O1—C112.8 (2)
O1—C8—C9—C10179.81 (15)C7—C8—O1—C11−177.55 (15)
C7—C8—C9—C100.1 (3)C12—C11—O1—C8−178.33 (13)
C6—C5—C10—C9−1.3 (2)N1—C4—O2—C1−176.74 (14)
N1—C5—C10—C9179.71 (14)C3—C4—O2—C12.39 (18)
C8—C9—C10—C51.0 (3)C2—C1—O2—C40.15 (18)
O1—C11—C12—C17−104.90 (19)O4—C18—O5—C19−0.9 (2)
O1—C11—C12—C1375.5 (2)C3—C18—O5—C19178.40 (16)
C17—C12—C13—C14−0.3 (3)C20—C19—O5—C18−168.96 (18)
C11—C12—C13—C14179.31 (17)
D—H···AD—HH···AD···AD—H···A
N1—H1···O40.862.122.7485 (15)129
C6—H6···O3i0.932.513.3951 (18)160
C17—H17···O4ii0.932.583.465 (2)160
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O40.862.122.7485 (15)129
C6—H6⋯O3i0.932.513.3951 (18)160
C17—H17⋯O4ii0.932.583.465 (2)160

Symmetry codes: (i) ; (ii) .

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