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ISSN: 2056-9890

(E)-5-(2-Nitro­prop-1-en­yl)-2,3-di­hydro-1-benzo­furan

aDepartment of Chemical Engineering, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China, and bDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China
*Correspondence e-mail: njutshs@126.com

(Received 6 May 2009; accepted 17 June 2009; online 27 June 2009)

The asymmetric unit of the title compound, C11H11NO3, contains two crystallographically independent mol­ecules. The aromatic rings are oriented at a dihedral angle of 56.17 (5)°. The furan rings adopt envelope conformations. Intra­molecular C—H⋯N inter­actions results in the formation of two six-membered rings with twisted conformations. In the crystal structure, three weak C—H⋯π inter­actions are found.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11NO3

  • Mr = 205.21

  • Monoclinic, P 21

  • a = 6.1280 (12) Å

  • b = 15.369 (3) Å

  • c = 11.193 (2) Å

  • β = 101.38 (3)°

  • V = 1033.5 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 294 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.981, Tmax = 0.990

  • 2548 measured reflections

  • 2335 independent reflections

  • 1289 reflections with I > 2σ(I)

  • Rint = 0.031

  • 3 standard reflections frequency: 120 min intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.163

  • S = 1.01

  • 2335 reflections

  • 271 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7A⋯N1 0.93 2.58 3.096 (8) 116
C18—H18A⋯N2 0.93 2.60 3.094 (7) 114
C4—H4ACg4 0.97 2.88 3.673 (8) 140
C8—H8ACg3i 0.93 2.92 3.578 (8) 129
C15—H15BCg2 0.97 2.85 3.636 (7) 139
C19—H19ACg2ii 0.93 2.75 3.497 (7) 139
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) [-x+2, y-{\script{1\over 2}}, -z+1]. Cg2, Cg3 and Cg4 are the centroids of the C2/C3/C5–C8, O4/C12–C15 and C13/C14/C16–C19 rings, respectively.

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information


Comment top

Some derivatives of benzol are important chemical materials. We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings B (C2/C3/C5-C8) and D (C13/C14/C16-C19) are, of course, planar and the dihedral angle between them is B/D = 56.17 (5)°. Rings A (O1/C1-C4) and C (O4/C12-C15) adopt envelope conformations with atoms C1 and C12 displaced by -0.189 (4) and -0.124 (5) Å from the planes of the other rings atoms. The moieties E (N1/C9-C11) and F (N2/C20-C22) are planar [the maximum deviations are -0.002 (4) and 0.016 (4) Å for atoms C10 and C21, respectively], and they are oriented with respect to the adjacent rings at dihedral angles of B/E = 32.39 (4) and D/F = 35.26 (5) °. Intramolecular C-H···N interactions (Table 1) results in the formations of two six-membered rings (N1/C6/C7/C9/C10/H7A) and (N2/C17/C18/C20/C21/H18A) having twisted conformations.

In the crystal structure, three weak C—H···π interactions are found.

Related literature top

For bond-length data, see: Allen et al. (1987). Cg2, Cg3 and Cg4 are the centroids of the C2/C3/C5–C8, O4/C12–C15 and C13/C14/C16–C19 rings, respectively.

Experimental top

For the preparation of the title compound, ammonium acetate (0.92 g, 12 mmol) was added to a solution of 5-formyl-2,3-dihydrobenzofuran (3.3 g, 22.3 mmol) in nitroethane (10 ml). The mixture was heated with stirring to 383 K in an oil bath for 3.5 h. The volatiles were then removed by rotary evaporation. The crude product was triturated in cold CH3OH (10 ml), collected by filtration (yield; 3.06 g, 67%). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.

Refinement top

H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms. In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
(E)-5-(2-Nitroprop-1-enyl)-2,3-dihydro-1-benzofuran top
Crystal data top
C11H11NO3F(000) = 432
Mr = 205.21Dx = 1.319 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 6.1280 (12) Åθ = 10–13°
b = 15.369 (3) ŵ = 0.10 mm1
c = 11.193 (2) ÅT = 294 K
β = 101.38 (3)°Block, colorless
V = 1033.5 (4) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1289 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 27.0°, θmin = 1.9°
ω/2θ scansh = 07
Absorption correction: ψ scan
(North et al., 1968)
k = 019
Tmin = 0.981, Tmax = 0.990l = 1414
2548 measured reflections3 standard reflections every 120 min
2335 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.08P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2335 reflectionsΔρmax = 0.16 e Å3
271 parametersΔρmin = 0.14 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C11H11NO3V = 1033.5 (4) Å3
Mr = 205.21Z = 4
Monoclinic, P21Mo Kα radiation
a = 6.1280 (12) ŵ = 0.10 mm1
b = 15.369 (3) ÅT = 294 K
c = 11.193 (2) Å0.20 × 0.10 × 0.10 mm
β = 101.38 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1289 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.031
Tmin = 0.981, Tmax = 0.9903 standard reflections every 120 min
2548 measured reflections intensity decay: 1%
2335 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055271 parameters
wR(F2) = 0.163H-atom parameters constrained
S = 1.01Δρmax = 0.16 e Å3
2335 reflectionsΔρmin = 0.14 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7614 (7)0.4628 (3)0.6830 (3)0.0846 (13)
O20.2010 (8)0.4770 (4)0.0356 (4)0.1031 (16)
O30.2751 (6)0.3723 (3)0.1606 (4)0.0921 (14)
O40.2376 (7)0.6709 (3)0.6129 (4)0.0784 (14)
O50.3141 (7)0.6604 (4)0.0306 (5)0.1172 (19)
O60.2291 (7)0.7649 (3)0.0949 (4)0.0878 (13)
N10.3306 (7)0.4276 (3)0.0942 (5)0.0659 (13)
N20.1822 (7)0.7083 (3)0.0289 (4)0.0636 (12)
C10.9850 (13)0.4324 (5)0.7308 (6)0.098 (2)
H1A0.98280.39020.79500.118*
H1B1.07830.48080.76510.118*
C20.9084 (8)0.4194 (3)0.5194 (5)0.0548 (13)
C30.7336 (8)0.4598 (4)0.5594 (5)0.0563 (15)
C41.0773 (10)0.3913 (5)0.6293 (5)0.0720 (16)
H4A1.08370.32850.63690.086*
H4B1.22440.41350.62650.086*
C50.9035 (8)0.4120 (3)0.3964 (5)0.0540 (14)
H5A1.02070.38560.36870.065*
C60.7209 (7)0.4443 (3)0.3137 (5)0.0490 (12)
C70.5452 (8)0.4844 (4)0.3565 (5)0.0550 (14)
H7A0.42360.50600.30140.066*
C80.5529 (9)0.4917 (4)0.4809 (5)0.0621 (14)
H8A0.43700.51790.51010.074*
C90.7270 (8)0.4392 (4)0.1835 (5)0.0627 (16)
H9A0.86990.43890.16700.075*
C100.5669 (9)0.4350 (4)0.0849 (5)0.0624 (15)
C110.5970 (10)0.4375 (5)0.0440 (6)0.084 (2)
H11A0.75250.44240.04560.126*
H11B0.51880.48660.08460.126*
H11C0.53900.38490.08470.126*
C120.4566 (12)0.7054 (5)0.6645 (5)0.086 (2)
H12A0.55190.65920.70460.103*
H12B0.44490.74980.72440.103*
C130.3874 (8)0.7151 (4)0.4498 (5)0.0555 (15)
C140.2113 (8)0.6758 (4)0.4893 (5)0.0546 (13)
C150.5551 (9)0.7439 (4)0.5618 (5)0.0687 (16)
H15A0.70200.72050.56140.082*
H15B0.56400.80690.56740.082*
C160.3809 (8)0.7200 (4)0.3276 (5)0.0590 (14)
H16A0.49960.74530.30010.071*
C170.2018 (8)0.6882 (4)0.2430 (5)0.0512 (13)
C180.0343 (9)0.6479 (3)0.2890 (5)0.0588 (14)
H18A0.08430.62410.23390.071*
C190.0323 (9)0.6409 (4)0.4116 (5)0.0617 (16)
H19A0.08390.61410.43970.074*
C200.2089 (8)0.6926 (4)0.1136 (5)0.0617 (14)
H20A0.35220.69170.09780.074*
C210.0500 (8)0.6977 (4)0.0139 (5)0.0609 (15)
C220.0741 (11)0.6899 (6)0.1155 (5)0.096 (2)
H22A0.22860.68340.11870.144*
H22B0.01630.74130.15930.144*
H22C0.00720.64000.15180.144*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.106 (3)0.093 (3)0.061 (3)0.016 (3)0.032 (2)0.002 (2)
O20.077 (3)0.119 (4)0.110 (4)0.027 (3)0.012 (3)0.014 (3)
O30.070 (3)0.107 (4)0.104 (3)0.020 (3)0.028 (2)0.014 (3)
O40.090 (3)0.088 (4)0.057 (2)0.010 (3)0.015 (2)0.004 (2)
O50.064 (2)0.164 (5)0.117 (4)0.025 (3)0.002 (3)0.039 (4)
O60.081 (3)0.091 (3)0.096 (3)0.032 (3)0.026 (2)0.004 (3)
N10.052 (3)0.070 (3)0.076 (3)0.001 (3)0.015 (2)0.002 (3)
N20.057 (3)0.074 (3)0.057 (3)0.002 (3)0.004 (2)0.004 (3)
C10.109 (5)0.110 (6)0.073 (5)0.025 (5)0.010 (4)0.006 (4)
C20.060 (3)0.048 (3)0.058 (3)0.005 (3)0.014 (3)0.007 (3)
C30.062 (4)0.051 (4)0.062 (4)0.004 (3)0.026 (3)0.010 (3)
C40.065 (3)0.074 (4)0.074 (4)0.011 (3)0.008 (3)0.015 (3)
C50.047 (3)0.049 (3)0.066 (4)0.009 (3)0.012 (3)0.002 (3)
C60.038 (2)0.051 (3)0.058 (3)0.000 (2)0.009 (2)0.002 (2)
C70.040 (3)0.048 (3)0.081 (4)0.009 (2)0.023 (3)0.009 (3)
C80.064 (3)0.056 (4)0.073 (4)0.013 (3)0.031 (3)0.002 (3)
C90.046 (3)0.073 (4)0.070 (4)0.002 (3)0.013 (3)0.007 (3)
C100.059 (3)0.069 (4)0.063 (3)0.002 (3)0.023 (3)0.004 (3)
C110.079 (4)0.108 (6)0.066 (4)0.019 (4)0.016 (3)0.001 (4)
C120.121 (6)0.080 (5)0.053 (4)0.014 (4)0.006 (4)0.006 (4)
C130.048 (3)0.048 (4)0.071 (4)0.005 (3)0.013 (3)0.005 (3)
C140.056 (3)0.052 (3)0.056 (3)0.000 (3)0.013 (3)0.004 (3)
C150.057 (3)0.081 (4)0.063 (4)0.004 (3)0.000 (3)0.007 (3)
C160.056 (3)0.061 (4)0.066 (3)0.002 (3)0.028 (3)0.004 (3)
C170.044 (3)0.053 (3)0.057 (3)0.002 (3)0.011 (2)0.000 (3)
C180.064 (3)0.051 (3)0.061 (3)0.003 (3)0.012 (3)0.006 (3)
C190.058 (3)0.057 (4)0.070 (4)0.007 (3)0.012 (3)0.009 (3)
C200.043 (2)0.079 (4)0.065 (3)0.004 (3)0.016 (2)0.000 (3)
C210.052 (3)0.066 (4)0.068 (3)0.004 (3)0.021 (2)0.002 (3)
C220.095 (4)0.138 (7)0.060 (4)0.028 (5)0.028 (3)0.005 (4)
Geometric parameters (Å, º) top
N1—O21.197 (6)C11—H11A0.9600
N1—O31.221 (6)C11—H11B0.9600
N1—C101.476 (7)C11—H11C0.9600
N2—O51.194 (6)C12—O41.452 (8)
N2—O61.211 (6)C12—H12A0.9700
N2—C211.475 (7)C12—H12B0.9700
C1—O11.446 (8)C13—C161.363 (7)
C1—H1A0.9700C13—C141.383 (7)
C1—H1B0.9700C14—O41.363 (6)
C2—C51.375 (7)C14—C191.368 (7)
C2—C31.386 (7)C15—C121.521 (8)
C3—O11.362 (6)C15—C131.521 (7)
C3—C81.362 (7)C15—H15A0.9700
C4—C11.505 (9)C15—H15B0.9700
C4—C21.506 (7)C16—C171.389 (7)
C4—H4A0.9700C16—H16A0.9300
C4—H4B0.9700C17—C181.383 (7)
C5—C61.395 (7)C17—C201.458 (7)
C5—H5A0.9300C18—C191.379 (7)
C6—C71.404 (6)C18—H18A0.9300
C6—C91.468 (7)C19—H19A0.9300
C7—C81.389 (7)C20—C211.331 (7)
C7—H7A0.9300C20—H20A0.9300
C8—H8A0.9300C21—C221.489 (8)
C9—C101.325 (7)C22—H22A0.9600
C9—H9A0.9300C22—H22B0.9600
C10—C111.490 (7)C22—H22C0.9600
C3—O1—C1106.5 (4)H11A—C11—H11B109.5
C14—O4—C12107.4 (4)C10—C11—H11C109.5
O2—N1—O3122.7 (5)H11A—C11—H11C109.5
O2—N1—C10117.9 (5)H11B—C11—H11C109.5
O3—N1—C10119.4 (5)O4—C12—C15108.3 (5)
O5—N2—O6124.5 (5)O4—C12—H12A110.0
O5—N2—C21115.5 (5)C15—C12—H12A110.0
O6—N2—C21120.0 (5)O4—C12—H12B110.0
O1—C1—C4109.0 (5)C15—C12—H12B110.0
O1—C1—H1A109.9H12A—C12—H12B108.4
C4—C1—H1A109.9C16—C13—C14118.3 (5)
O1—C1—H1B109.9C16—C13—C15133.8 (5)
C4—C1—H1B109.9C14—C13—C15107.9 (5)
H1A—C1—H1B108.3O4—C14—C19122.9 (5)
C5—C2—C3119.6 (5)O4—C14—C13113.9 (5)
C5—C2—C4132.0 (5)C19—C14—C13123.1 (5)
C3—C2—C4108.4 (5)C12—C15—C13101.8 (5)
O1—C3—C8124.4 (5)C12—C15—H15A111.4
O1—C3—C2113.2 (5)C13—C15—H15A111.4
C8—C3—C2122.4 (5)C12—C15—H15B111.4
C1—C4—C2101.3 (5)C13—C15—H15B111.4
C1—C4—H4A111.5H15A—C15—H15B109.3
C2—C4—H4A111.5C13—C16—C17121.9 (5)
C1—C4—H4B111.5C13—C16—H16A119.1
C2—C4—H4B111.5C17—C16—H16A119.1
H4A—C4—H4B109.3C18—C17—C16116.6 (5)
C2—C5—C6119.4 (5)C18—C17—C20124.1 (5)
C2—C5—H5A120.3C16—C17—C20119.1 (4)
C6—C5—H5A120.3C19—C18—C17124.0 (5)
C5—C6—C7119.9 (5)C19—C18—H18A118.0
C5—C6—C9117.8 (4)C17—C18—H18A118.0
C7—C6—C9122.2 (5)C14—C19—C18116.0 (5)
C8—C7—C6120.1 (5)C14—C19—H19A122.0
C8—C7—H7A120.0C18—C19—H19A122.0
C6—C7—H7A120.0C21—C20—C17132.5 (5)
C3—C8—C7118.7 (5)C21—C20—H20A113.8
C3—C8—H8A120.7C17—C20—H20A113.8
C7—C8—H8A120.7C20—C21—N2118.3 (5)
C10—C9—C6132.0 (5)C20—C21—C22127.9 (5)
C10—C9—H9A114.0N2—C21—C22113.7 (5)
C6—C9—H9A114.0C21—C22—H22A109.5
C9—C10—N1121.4 (5)C21—C22—H22B109.5
C9—C10—C11126.3 (6)H22A—C22—H22B109.5
N1—C10—C11112.4 (5)C21—C22—H22C109.5
C10—C11—H11A109.5H22A—C22—H22C109.5
C10—C11—H11B109.5H22B—C22—H22C109.5
C2—C3—O1—C17.9 (7)C7—C6—C9—C1030.1 (10)
C4—C1—O1—C312.6 (7)C6—C7—C8—C30.3 (8)
C8—C3—O1—C1172.9 (6)C6—C9—C10—N15.0 (11)
O2—N1—C10—C9129.9 (6)C6—C9—C10—C11174.6 (6)
O3—N1—C10—C949.9 (8)C15—C12—O4—C147.6 (7)
O2—N1—C10—C1149.8 (7)C15—C13—C14—O42.1 (6)
O3—N1—C10—C11130.4 (6)C15—C13—C14—C19178.9 (5)
O5—N2—C21—C20131.9 (6)C16—C13—C14—O4177.5 (5)
O5—N2—C21—C2245.6 (8)C16—C13—C14—C190.7 (8)
O6—N2—C21—C2050.6 (8)C14—C13—C16—C171.2 (8)
O6—N2—C21—C22132.0 (6)C15—C13—C16—C17179.4 (6)
C5—C2—C3—O1179.7 (5)C19—C14—O4—C12173.4 (6)
C4—C2—C3—O10.1 (7)C13—C14—O4—C123.5 (6)
C5—C2—C3—C81.0 (8)O4—C14—C19—C18177.4 (5)
C4—C2—C3—C8179.3 (6)C13—C14—C19—C180.8 (8)
C3—C2—C5—C60.8 (8)C13—C15—C12—O48.3 (7)
C4—C2—C5—C6179.7 (6)C12—C15—C13—C146.3 (6)
O1—C3—C8—C7180.0 (5)C12—C15—C13—C16173.2 (6)
C2—C3—C8—C70.8 (8)C13—C16—C17—C182.7 (8)
C2—C4—C1—O112.0 (7)C13—C16—C17—C20177.7 (5)
C1—C4—C2—C5172.3 (6)C16—C17—C18—C192.6 (8)
C1—C4—C2—C37.3 (7)C20—C17—C18—C19177.4 (5)
C2—C5—C6—C70.4 (8)C18—C17—C20—C2132.8 (10)
C2—C5—C6—C9176.9 (5)C16—C17—C20—C21152.5 (7)
C5—C6—C7—C80.1 (8)C17—C18—C19—C140.9 (8)
C9—C6—C7—C8176.5 (5)C17—C20—C21—N26.0 (10)
C5—C6—C9—C10153.4 (7)C17—C20—C21—C22171.0 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···N10.932.583.096 (8)116
C18—H18A···N20.932.603.094 (7)114
C4—H4A···Cg40.972.883.673 (8)140
C8—H8A···Cg3i0.932.923.578 (8)129
C15—H15B···Cg20.972.853.636 (7)139
C19—H19A···Cg2ii0.932.753.497 (7)139
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+2, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC11H11NO3
Mr205.21
Crystal system, space groupMonoclinic, P21
Temperature (K)294
a, b, c (Å)6.1280 (12), 15.369 (3), 11.193 (2)
β (°) 101.38 (3)
V3)1033.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.981, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
2548, 2335, 1289
Rint0.031
(sin θ/λ)max1)0.638
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.163, 1.01
No. of reflections2335
No. of parameters271
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.14

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···N10.932.583.096 (8)116
C18—H18A···N20.932.603.094 (7)114
C4—H4A···Cg40.972.883.673 (8)140
C8—H8A···Cg3i0.932.923.578 (8)129
C15—H15B···Cg20.972.853.636 (7)139
C19—H19A···Cg2ii0.932.753.497 (7)139
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+2, y1/2, z+1.
 

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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