Literature DB >> 21578858

3-(1-Naphth-yl)-N-phenyl-oxirane-2-carboxamide.

Lian-Mei Chen1, Tai-Ran Kang.   

Abstract

In the title compound, C(19)H(15)NO(2), the mol-ecule adopts a syn configuration with the naphthalene and N-phenyl-formamide units located on the same side of the ep-oxy ring. The ep-oxy ring makes dihedral angles of 58.73 (9) and 65.18 (9)°, respectively, with the naphthalene ring system and the benzene ring. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonding is present in the crystal structure.

Entities:  

Year:  2009        PMID： 21578858      PMCID： PMC2971758          DOI： 10.1107/S1600536809048752

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


Related literature

For background to the use of epoxide-containing compounds as building blocks in the synthesis of biologically active compounds, see: Porter & Skidmore (2000 ▶); Shing et al. (2006 ▶); Watanabe et al. (1998 ▶). For related structures, see: He (2009 ▶); He & Chen (2009 ▶); He et al. (2009 ▶).

Experimental

Crystal data

C19H15NO2 M = 289.32 Orthorhombic, a = 6.62890 (10) Å b = 10.03500 (10) Å c = 23.2033 (3) Å V = 1543.51 (3) Å3 Z = 4 Cu Kα radiation μ = 0.65 mm−1 T = 290 K 0.40 × 0.36 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.782, T max = 0.829 13761 measured reflections 1783 independent reflections 1641 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.093 S = 1.08 1783 reflections 203 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.08 e Å−3 Δρmin = −0.13 e Å−3 Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048752/xu2678sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048752/xu2678Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H15NO2F(000) = 608
Mr = 289.32Dx = 1.245 Mg m−3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2abCell parameters from 9381 reflections
a = 6.6289 (1) Åθ = 3.8–72.1°
b = 10.0350 (1) ŵ = 0.65 mm−1
c = 23.2033 (3) ÅT = 290 K
V = 1543.51 (3) Å3Block, colorless
Z = 40.40 × 0.36 × 0.30 mm
Oxford Diffraction Gemini S Ultra diffractometer1783 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source1641 reflections with I > 2σ(I)
mirrorRint = 0.031
Detector resolution: 15.9149 pixels mm-1θmax = 72.3°, θmin = 3.8°
ω scansh = −6→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −12→12
Tmin = 0.782, Tmax = 0.829l = −26→28
13761 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0641P)2 + 0.0314P] where P = (Fo2 + 2Fc2)/3
1783 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.08 e Å−3
0 restraintsΔρmin = −0.13 e Å−3
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
O11.20270 (19)0.10810 (12)0.82723 (5)0.0681 (3)
O21.0096 (2)0.38001 (11)0.74225 (7)0.0738 (4)
N10.8951 (2)0.16688 (13)0.74912 (6)0.0534 (3)
H40.926 (3)0.092 (2)0.7622 (8)0.065 (5)*
C10.3564 (3)0.1625 (3)0.65510 (8)0.0820 (6)
H10.23760.15920.63390.098*
C20.4104 (3)0.0578 (2)0.68938 (9)0.0750 (5)
H20.3275−0.01680.69170.090*
C30.5874 (3)0.06219 (17)0.72067 (8)0.0619 (4)
H30.6224−0.00900.74430.074*
C40.7135 (2)0.17226 (15)0.71700 (6)0.0521 (3)
C50.6590 (3)0.27941 (19)0.68282 (8)0.0659 (4)
H50.74110.35430.68040.079*
C60.4786 (3)0.2728 (2)0.65216 (9)0.0806 (6)
H60.44020.34450.62920.097*
C71.0258 (2)0.26612 (14)0.75961 (7)0.0523 (3)
C81.2046 (2)0.23071 (15)0.79612 (7)0.0558 (4)
H81.33590.25730.78050.067*
C91.1896 (2)0.23005 (17)0.85940 (8)0.0597 (4)
H91.31350.25550.87970.072*
C100.9999 (3)0.25565 (18)0.89182 (7)0.0588 (4)
C110.8539 (3)0.1600 (2)0.89662 (8)0.0738 (5)
H110.86890.07910.87760.089*
C120.6808 (3)0.1835 (3)0.93030 (9)0.0855 (7)
H120.58190.11810.93300.103*
C130.6567 (3)0.2994 (3)0.95855 (9)0.0854 (7)
H130.54140.31270.98070.103*
C140.8028 (3)0.4013 (2)0.95534 (7)0.0718 (5)
C150.9780 (3)0.38002 (19)0.92061 (7)0.0587 (4)
C161.1212 (3)0.4825 (2)0.91701 (8)0.0690 (4)
H161.23450.47100.89390.083*
C171.0979 (4)0.5988 (3)0.94673 (10)0.0880 (6)
H171.19380.66590.94320.106*
C180.9322 (5)0.6176 (3)0.98222 (11)0.1012 (8)
H180.92050.69561.00360.121*
C190.7874 (4)0.5231 (3)0.98595 (9)0.0927 (7)
H190.67520.53831.00910.111*
U11U22U33U12U13U23
O10.0674 (7)0.0523 (6)0.0846 (7)0.0119 (6)−0.0146 (6)−0.0057 (5)
O20.0694 (7)0.0412 (6)0.1109 (10)−0.0041 (6)−0.0195 (7)0.0016 (6)
N10.0506 (7)0.0396 (6)0.0700 (7)−0.0001 (5)−0.0054 (6)−0.0003 (6)
C10.0604 (10)0.1084 (17)0.0771 (11)0.0011 (11)−0.0134 (9)−0.0229 (12)
C20.0523 (9)0.0768 (12)0.0960 (13)−0.0071 (9)0.0031 (9)−0.0250 (11)
C30.0518 (8)0.0524 (8)0.0814 (10)−0.0007 (7)0.0049 (7)−0.0099 (8)
C40.0486 (8)0.0488 (7)0.0590 (8)0.0025 (7)0.0020 (6)−0.0085 (6)
C50.0660 (10)0.0609 (9)0.0707 (9)−0.0014 (8)−0.0075 (8)0.0042 (8)
C60.0768 (12)0.0928 (14)0.0722 (11)0.0095 (12)−0.0161 (10)0.0058 (10)
C70.0491 (8)0.0411 (7)0.0666 (8)0.0019 (6)−0.0003 (7)−0.0092 (6)
C80.0455 (7)0.0464 (7)0.0754 (9)0.0041 (7)−0.0016 (7)−0.0099 (7)
C90.0476 (8)0.0591 (8)0.0725 (9)0.0031 (7)−0.0106 (7)−0.0094 (7)
C100.0505 (8)0.0687 (9)0.0571 (8)0.0000 (8)−0.0086 (7)0.0031 (7)
C110.0653 (10)0.0803 (12)0.0757 (10)−0.0129 (10)−0.0124 (9)0.0083 (10)
C120.0612 (11)0.1093 (17)0.0859 (13)−0.0194 (13)−0.0057 (10)0.0263 (13)
C130.0564 (11)0.131 (2)0.0693 (10)0.0054 (12)0.0082 (9)0.0238 (12)
C140.0595 (10)0.1020 (14)0.0539 (8)0.0149 (11)0.0018 (7)0.0095 (9)
C150.0531 (8)0.0723 (10)0.0505 (7)0.0054 (8)−0.0034 (6)0.0030 (7)
C160.0660 (10)0.0751 (11)0.0658 (9)−0.0003 (9)−0.0002 (8)−0.0080 (9)
C170.0988 (16)0.0799 (13)0.0853 (12)−0.0038 (13)−0.0017 (12)−0.0181 (11)
C180.120 (2)0.1003 (17)0.0831 (13)0.0244 (18)0.0033 (14)−0.0278 (13)
C190.0897 (15)0.1226 (19)0.0658 (10)0.0355 (16)0.0118 (11)−0.0050 (12)
O1—C81.4266 (19)C9—C101.488 (2)
O1—C91.436 (2)C9—H90.9800
O2—C71.217 (2)C10—C111.367 (3)
N1—C71.342 (2)C10—C151.423 (2)
N1—C41.417 (2)C11—C121.408 (3)
N1—H40.84 (2)C11—H110.9300
C1—C21.365 (3)C12—C131.345 (4)
C1—C61.373 (3)C12—H120.9300
C1—H10.9300C13—C141.410 (3)
C2—C31.381 (3)C13—H130.9300
C2—H20.9300C14—C191.417 (4)
C3—C41.388 (2)C14—C151.429 (2)
C3—H30.9300C15—C161.402 (3)
C4—C51.384 (2)C16—C171.364 (3)
C5—C61.393 (3)C16—H160.9300
C5—H50.9300C17—C181.386 (4)
C6—H60.9300C17—H170.9300
C7—C81.499 (2)C18—C191.352 (4)
C8—C91.472 (2)C18—H180.9300
C8—H80.9800C19—H190.9300
C8—O1—C961.87 (10)O1—C9—H9114.9
C7—N1—C4127.99 (14)C8—C9—H9114.9
C7—N1—H4116.1 (15)C10—C9—H9114.9
C4—N1—H4115.8 (15)C11—C10—C15120.32 (16)
C2—C1—C6119.65 (18)C11—C10—C9121.23 (17)
C2—C1—H1120.2C15—C10—C9118.36 (15)
C6—C1—H1120.2C10—C11—C12120.3 (2)
C1—C2—C3120.29 (19)C10—C11—H11119.8
C1—C2—H2119.9C12—C11—H11119.8
C3—C2—H2119.9C13—C12—C11120.8 (2)
C2—C3—C4120.33 (18)C13—C12—H12119.6
C2—C3—H3119.8C11—C12—H12119.6
C4—C3—H3119.8C12—C13—C14121.31 (19)
C5—C4—C3119.75 (15)C12—C13—H13119.3
C5—C4—N1123.56 (15)C14—C13—H13119.3
C3—C4—N1116.68 (14)C13—C14—C19123.3 (2)
C4—C5—C6118.67 (18)C13—C14—C15118.65 (19)
C4—C5—H5120.7C19—C14—C15118.0 (2)
C6—C5—H5120.7C16—C15—C10123.11 (16)
C1—C6—C5121.3 (2)C16—C15—C14118.30 (18)
C1—C6—H6119.4C10—C15—C14118.59 (17)
C5—C6—H6119.4C17—C16—C15121.4 (2)
O2—C7—N1125.45 (15)C17—C16—H16119.3
O2—C7—C8118.66 (14)C15—C16—H16119.3
N1—C7—C8115.89 (13)C16—C17—C18120.5 (2)
O1—C8—C959.38 (10)C16—C17—H17119.8
O1—C8—C7118.91 (13)C18—C17—H17119.8
C9—C8—C7120.76 (13)C19—C18—C17120.4 (2)
O1—C8—H8115.4C19—C18—H18119.8
C9—C8—H8115.4C17—C18—H18119.8
C7—C8—H8115.4C18—C19—C14121.4 (2)
O1—C9—C858.75 (10)C18—C19—H19119.3
O1—C9—C10117.46 (15)C14—C19—H19119.3
C8—C9—C10124.10 (14)
C6—C1—C2—C3−0.4 (3)O1—C9—C10—C15−175.59 (13)
C1—C2—C3—C4−0.8 (3)C8—C9—C10—C15−106.34 (18)
C2—C3—C4—C51.5 (2)C15—C10—C11—C12−0.3 (3)
C2—C3—C4—N1−178.11 (15)C9—C10—C11—C12176.26 (16)
C7—N1—C4—C511.2 (2)C10—C11—C12—C13−0.5 (3)
C7—N1—C4—C3−169.22 (16)C11—C12—C13—C140.2 (3)
C3—C4—C5—C6−0.9 (3)C12—C13—C14—C19−177.7 (2)
N1—C4—C5—C6178.69 (16)C12—C13—C14—C150.8 (3)
C2—C1—C6—C51.0 (3)C11—C10—C15—C16−179.42 (17)
C4—C5—C6—C1−0.4 (3)C9—C10—C15—C164.0 (2)
C4—N1—C7—O2−0.7 (3)C11—C10—C15—C141.2 (2)
C4—N1—C7—C8179.01 (13)C9—C10—C15—C14−175.40 (14)
C9—O1—C8—C7−110.62 (15)C13—C14—C15—C16179.15 (17)
O2—C7—C8—O1165.96 (15)C19—C14—C15—C16−2.3 (2)
N1—C7—C8—O1−13.7 (2)C13—C14—C15—C10−1.5 (2)
O2—C7—C8—C996.3 (2)C19—C14—C15—C10177.07 (16)
N1—C7—C8—C9−83.36 (18)C10—C15—C16—C17−177.89 (18)
C8—O1—C9—C10115.07 (16)C14—C15—C16—C171.5 (3)
C7—C8—C9—O1107.55 (15)C15—C16—C17—C181.1 (4)
O1—C8—C9—C10−103.91 (18)C16—C17—C18—C19−2.7 (4)
C7—C8—C9—C103.6 (2)C17—C18—C19—C141.8 (4)
O1—C9—C10—C117.8 (2)C13—C14—C19—C18179.2 (2)
C8—C9—C10—C1177.1 (2)C15—C14—C19—C180.7 (3)
D—H···AD—HH···AD···AD—H···A
N1—H4···O2i0.84 (2)2.17 (2)2.954 (1)155.7 (18)
C5—H5···O1ii0.932.583.431 (2)153 (1)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H4⋯O2i 0.84 (2)2.17 (2)2.954 (1)155.7 (18)
C5—H5⋯O1ii 0.932.583.431 (2)153 (1)

Symmetry codes: (i) ; (ii) .

  4 in total

1.  A short history of SHELX.

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

2.  3-(3-Chloro-phen-yl)-N-phenyl-oxirane-2-carboxamide.

Authors:  Long He; Lian-Mei Chen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-04

3.  3-(2-Bromo-phen-yl)-N-phenyl-oxirane-2-carboxamide.

Authors:  Long He; Hong-Mei Qin; Lian-Mei Chen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-04

4.  3-(4-Nitro-phen-yl)-N-phenyl-oxirane-2-carboxamide.

Authors:  Long He
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-31
  4 in total
  1 in total

1.  3-(3-Cyano-phen-yl)-N-phenyl-oxirane-2-carboxamide.

Authors:  Tai-Ran Kang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-25
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.