organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1,3-Bis(4-tert-butyl­phen­yl)-4-nitro­butan-1-one

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 25 March 2011; accepted 13 May 2011; online 20 May 2011)

In the crystal structure of the title compound, C24H31NO3, mol­ecules are connected via C—H⋯O inter­molecular hydrogen bonds, forming dimers. The benzene rings are oriented at a dihedral angle of 29.8 (1)°.

Related literature

For applications of the title compound, see: Gorman et al. (2004[Gorman, A., Killoran, J., Oshea, C., Kenna, T., Gallagher, W. M. & Oshea, D. F. (2004). J. Am. Chem. Soc. 126, 10619-10631.]). For a related structure, see: Hall et al. (2005[Hall, M. J., McDonnell, S. O., Killoran, J. & Oshea, D. F. (2005). J. Org. Chem. 70, 5571-5578.]). For the synthesis of the title compound, see: Liang et al. (2006[Liang, Y. J., Dong, D. W., Lu, Y. M., Wang, Y., Pan, W., Chai, Y. Y. & Liu, Q. (2006). Synthesis, 19, 3301-3304.]). 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
  • C24H31NO3

  • Mr = 381.50

  • Orthorhombic, P n a 21

  • a = 20.440 (4) Å

  • b = 17.500 (4) Å

  • c = 6.1630 (12) Å

  • V = 2204.5 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 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 = 0.985, Tmax = 0.993

  • 8662 measured reflections

  • 2247 independent reflections

  • 1527 reflections with I > 2σ(I)

  • Rint = 0.096

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.181

  • S = 1.00

  • 2247 reflections

  • 247 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12A⋯O1i 0.97 2.52 3.072 (5) 116
Symmetry code: (i) [-x+1, -y+1, z+{\script{1\over 2}}].

Data collection: CAD-4 Software (Enraf-Nonius, 1985[Enraf-Nonius (1985). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The tittle compound, 1,3-bis(4-tert-butylphenyl)-4-nitrobutan-1-one is an important intermediate (Gorman et al., 2004) for the synthesis of 2,4-bis(4-tert-butylphenyl)-4-oxobutanal, which can be used to synthesis 2,4-bis(4-tert-butylphenyl)-1H-pyrrole(Hall et al., 2005). We report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the rings (C5—C10) and (C15—C20) is 29.8 (1)°. The bond lengths and angles are within normal ranges (Allen et al., 1987).

The molecules of (I) were connected together via C—H···O intermolecular hydrogen bonds to form molecular dimers (Table 1. and Fig. 2.).

Related literature top

For applications of the title compound, see: Gorman et al. (2004). For a related structure, see: Hall et al. (2005). For the synthesis of the title compound, see: Liang et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I) was prepared by the method of Michael reaction reported in literature (Liang et al., 2006). The crystals were obtained by dissolving (I) (0.2 g, 0.52 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 5 d.

Refinement top

H atoms were positioned geometrically and refined as riding groups, with C—H = 0.93, 0.96, 0.97 and 0.98 Å for aromatic, methyl, methylene and methine H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.2 for aromatic H, and x = 1.5 for other H.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1985); cell refinement: CAD-4 Software (Enraf-Nonius, 1985); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
1,3-Bis(4-tert-butylphenyl)-4-nitrobutan-1-one top
Crystal data top
C24H31NO3F(000) = 824
Mr = 381.50Dx = 1.149 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 25 reflections
a = 20.440 (4) Åθ = 9–13°
b = 17.500 (4) ŵ = 0.08 mm1
c = 6.1630 (12) ÅT = 293 K
V = 2204.5 (8) Å3Block, colourless
Z = 40.20 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.096
Graphite monochromatorθmax = 25.4°, θmin = 1.5°
ω/2θ scansh = 2424
Absorption correction: ψ scan
(North et al., 1968)
k = 2121
Tmin = 0.985, Tmax = 0.993l = 70
8662 measured reflections3 standard reflections every 200 reflections
2247 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
2247 reflections(Δ/σ)max < 0.001
247 parametersΔρmax = 0.35 e Å3
1 restraintΔρmin = 0.32 e Å3
Crystal data top
C24H31NO3V = 2204.5 (8) Å3
Mr = 381.50Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 20.440 (4) ŵ = 0.08 mm1
b = 17.500 (4) ÅT = 293 K
c = 6.1630 (12) Å0.20 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1527 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.096
Tmin = 0.985, Tmax = 0.9933 standard reflections every 200 reflections
8662 measured reflections intensity decay: 1%
2247 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0621 restraint
wR(F2) = 0.181H-atom parameters constrained
S = 1.00Δρmax = 0.35 e Å3
2247 reflectionsΔρmin = 0.32 e Å3
247 parameters
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
N0.6807 (2)0.5602 (3)0.0686 (7)0.0600 (11)
O10.50125 (15)0.54161 (17)0.2287 (6)0.0631 (10)
C10.4134 (3)0.9145 (3)0.5244 (13)0.0861 (15)
H1A0.38560.89490.41180.129*
H1B0.45640.92350.46690.129*
H1C0.39570.96150.57880.129*
O20.73656 (19)0.5582 (3)0.1435 (8)0.0888 (14)
C20.4638 (4)0.8985 (4)0.8758 (18)0.128 (4)
H2A0.44530.94650.91930.192*
H2B0.50630.90700.81360.192*
H2C0.46790.86581.00010.192*
O30.6580 (2)0.6145 (2)0.0204 (9)0.0976 (16)
C30.3532 (4)0.8505 (4)0.813 (2)0.141 (4)
H3A0.32210.82770.71620.211*
H3B0.33770.89990.85760.211*
H3C0.35850.81850.93850.211*
C40.4174 (3)0.8589 (3)0.7002 (13)0.0861 (15)
C50.4448 (2)0.7832 (3)0.6253 (9)0.0524 (12)
C60.4948 (2)0.7455 (3)0.7359 (9)0.0549 (12)
H6A0.51030.76600.86520.066*
C70.5216 (2)0.6792 (2)0.6595 (8)0.0505 (12)
H7A0.55520.65600.73690.061*
C80.49945 (19)0.6457 (2)0.4682 (8)0.0405 (10)
C90.4479 (2)0.6811 (3)0.3611 (10)0.0569 (13)
H9A0.43060.65940.23580.068*
C100.4224 (3)0.7479 (3)0.4400 (11)0.0654 (15)
H10A0.38820.77070.36440.078*
C110.5300 (2)0.5762 (2)0.3703 (8)0.0416 (10)
C120.5950 (2)0.5512 (2)0.4511 (8)0.0418 (10)
H12A0.59190.54200.60590.050*
H12B0.62600.59250.42950.050*
C130.6218 (2)0.4789 (2)0.3414 (8)0.0427 (11)
H13A0.58580.44200.34120.051*
C140.6395 (2)0.4918 (3)0.1035 (9)0.0530 (12)
H14A0.66260.44720.04970.064*
H14B0.59960.49710.01990.064*
C150.6768 (2)0.4417 (2)0.4692 (8)0.0435 (10)
C160.7202 (2)0.4823 (2)0.5969 (9)0.0453 (11)
H16A0.71720.53520.60260.054*
C170.76808 (19)0.4452 (2)0.7167 (9)0.0460 (11)
H17A0.79700.47420.79890.055*
C180.7743 (2)0.3668 (2)0.7183 (9)0.0466 (11)
C190.7315 (2)0.3266 (2)0.5847 (11)0.0605 (14)
H19A0.73580.27390.57320.073*
C200.6833 (2)0.3630 (2)0.4697 (10)0.0538 (12)
H20A0.65400.33380.38930.065*
C210.8267 (3)0.3263 (3)0.8525 (11)0.0643 (14)
C220.8825 (3)0.3032 (5)0.6997 (15)0.119 (3)
H22A0.91570.27700.78070.179*
H22B0.90080.34810.63420.179*
H22C0.86580.27000.58860.179*
C230.8533 (4)0.3767 (4)1.0330 (14)0.103 (3)
H23A0.81830.39111.12850.154*
H23B0.87250.42180.97130.154*
H23C0.88590.34911.11330.154*
C240.7971 (3)0.2562 (4)0.9646 (15)0.099 (2)
H24A0.76300.27221.06170.148*
H24B0.83050.23001.04500.148*
H24C0.77910.22240.85720.148*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.069 (3)0.076 (3)0.035 (2)0.006 (2)0.010 (2)0.002 (2)
O10.0523 (18)0.0704 (19)0.066 (2)0.0060 (16)0.0210 (19)0.028 (2)
C10.108 (3)0.061 (2)0.089 (4)0.013 (3)0.026 (3)0.002 (2)
O20.066 (2)0.131 (3)0.069 (3)0.036 (2)0.002 (2)0.011 (3)
C20.106 (5)0.105 (5)0.174 (10)0.027 (4)0.021 (7)0.067 (7)
O30.137 (4)0.071 (3)0.086 (3)0.005 (2)0.014 (4)0.026 (3)
C30.124 (6)0.083 (4)0.214 (12)0.017 (4)0.097 (8)0.004 (6)
C40.108 (3)0.061 (2)0.089 (4)0.013 (3)0.026 (3)0.002 (2)
C50.055 (3)0.046 (2)0.056 (3)0.002 (2)0.008 (3)0.003 (3)
C60.059 (3)0.058 (3)0.047 (3)0.014 (2)0.005 (3)0.008 (3)
C70.054 (3)0.056 (3)0.042 (3)0.005 (2)0.006 (2)0.005 (2)
C80.036 (2)0.045 (2)0.040 (2)0.0024 (17)0.001 (2)0.000 (2)
C90.055 (3)0.056 (3)0.060 (3)0.020 (2)0.017 (3)0.011 (3)
C100.063 (3)0.062 (3)0.071 (4)0.023 (3)0.016 (3)0.000 (3)
C110.041 (2)0.041 (2)0.043 (3)0.0027 (18)0.003 (2)0.000 (2)
C120.047 (2)0.046 (2)0.032 (2)0.0030 (18)0.012 (2)0.001 (2)
C130.041 (2)0.046 (2)0.041 (3)0.0016 (19)0.003 (2)0.002 (2)
C140.057 (3)0.063 (3)0.039 (3)0.001 (2)0.001 (3)0.005 (2)
C150.046 (2)0.042 (2)0.043 (3)0.0025 (18)0.011 (2)0.002 (2)
C160.054 (2)0.039 (2)0.042 (3)0.0018 (19)0.002 (2)0.003 (2)
C170.036 (2)0.056 (3)0.045 (3)0.0036 (18)0.008 (2)0.005 (3)
C180.041 (2)0.050 (2)0.049 (3)0.0076 (19)0.001 (2)0.001 (3)
C190.070 (3)0.037 (2)0.075 (4)0.003 (2)0.004 (3)0.008 (3)
C200.053 (3)0.041 (2)0.068 (3)0.002 (2)0.008 (3)0.013 (3)
C210.062 (3)0.066 (3)0.065 (3)0.014 (3)0.005 (3)0.014 (3)
C220.081 (4)0.160 (7)0.117 (7)0.070 (4)0.024 (5)0.044 (6)
C230.108 (5)0.096 (4)0.104 (6)0.003 (4)0.055 (5)0.004 (4)
C240.109 (5)0.084 (4)0.105 (6)0.001 (4)0.014 (5)0.042 (5)
Geometric parameters (Å, º) top
N—O31.192 (5)C12—H12A0.9700
N—O21.231 (5)C12—H12B0.9700
N—C141.479 (6)C13—C151.520 (6)
O1—C111.214 (5)C13—C141.527 (7)
C1—C41.457 (9)C13—H13A0.9800
C1—H1A0.9600C14—H14A0.9700
C1—H1B0.9600C14—H14B0.9700
C1—H1C0.9600C15—C161.381 (6)
C2—C41.597 (11)C15—C201.384 (6)
C2—H2A0.9600C16—C171.388 (6)
C2—H2B0.9600C16—H16A0.9300
C2—H2C0.9600C17—C181.377 (6)
C3—C41.493 (9)C17—H17A0.9300
C3—H3A0.9600C18—C191.392 (7)
C3—H3B0.9600C18—C211.528 (7)
C3—H3C0.9600C19—C201.371 (7)
C4—C51.511 (7)C19—H19A0.9300
C5—C101.377 (8)C20—H20A0.9300
C5—C61.394 (7)C21—C231.520 (9)
C6—C71.367 (6)C21—C241.533 (8)
C6—H6A0.9300C21—C221.533 (9)
C7—C81.392 (6)C22—H22A0.9600
C7—H7A0.9300C22—H22B0.9600
C8—C91.390 (6)C22—H22C0.9600
C8—C111.494 (6)C23—H23A0.9600
C9—C101.369 (6)C23—H23B0.9600
C9—H9A0.9300C23—H23C0.9600
C10—H10A0.9300C24—H24A0.9600
C11—C121.485 (6)C24—H24B0.9600
C12—C131.536 (6)C24—H24C0.9600
O3—N—O2123.9 (5)C15—C13—C14112.7 (4)
O3—N—C14119.3 (5)C15—C13—C12112.9 (4)
O2—N—C14116.8 (5)C14—C13—C12112.7 (4)
C4—C1—H1A109.5C15—C13—H13A105.9
C4—C1—H1B109.5C14—C13—H13A105.9
H1A—C1—H1B109.5C12—C13—H13A105.9
C4—C1—H1C109.5N—C14—C13113.2 (4)
H1A—C1—H1C109.5N—C14—H14A108.9
H1B—C1—H1C109.5C13—C14—H14A108.9
C4—C2—H2A109.5N—C14—H14B108.9
C4—C2—H2B109.5C13—C14—H14B108.9
H2A—C2—H2B109.5H14A—C14—H14B107.8
C4—C2—H2C109.5C16—C15—C20116.6 (4)
H2A—C2—H2C109.5C16—C15—C13123.4 (4)
H2B—C2—H2C109.5C20—C15—C13119.9 (4)
C4—C3—H3A109.5C15—C16—C17121.1 (4)
C4—C3—H3B109.5C15—C16—H16A119.5
H3A—C3—H3B109.5C17—C16—H16A119.5
C4—C3—H3C109.5C18—C17—C16122.3 (4)
H3A—C3—H3C109.5C18—C17—H17A118.8
H3B—C3—H3C109.5C16—C17—H17A118.8
C1—C4—C3111.3 (6)C17—C18—C19116.2 (4)
C1—C4—C5112.2 (6)C17—C18—C21122.1 (4)
C3—C4—C5112.4 (5)C19—C18—C21121.7 (4)
C1—C4—C2104.4 (6)C20—C19—C18121.5 (4)
C3—C4—C2104.4 (7)C20—C19—H19A119.2
C5—C4—C2111.5 (6)C18—C19—H19A119.2
C10—C5—C6115.9 (4)C19—C20—C15122.2 (5)
C10—C5—C4121.6 (5)C19—C20—H20A118.9
C6—C5—C4122.5 (5)C15—C20—H20A118.9
C7—C6—C5121.8 (5)C23—C21—C18112.2 (4)
C7—C6—H6A119.1C23—C21—C24106.0 (6)
C5—C6—H6A119.1C18—C21—C24109.8 (5)
C6—C7—C8121.2 (5)C23—C21—C22109.7 (6)
C6—C7—H7A119.4C18—C21—C22108.1 (5)
C8—C7—H7A119.4C24—C21—C22111.1 (5)
C9—C8—C7117.4 (4)C21—C22—H22A109.5
C9—C8—C11119.2 (4)C21—C22—H22B109.5
C7—C8—C11123.3 (4)H22A—C22—H22B109.5
C10—C9—C8120.1 (5)C21—C22—H22C109.5
C10—C9—H9A120.0H22A—C22—H22C109.5
C8—C9—H9A120.0H22B—C22—H22C109.5
C9—C10—C5123.4 (5)C21—C23—H23A109.5
C9—C10—H10A118.3C21—C23—H23B109.5
C5—C10—H10A118.3H23A—C23—H23B109.5
O1—C11—C12121.8 (4)C21—C23—H23C109.5
O1—C11—C8119.6 (4)H23A—C23—H23C109.5
C12—C11—C8118.6 (4)H23B—C23—H23C109.5
C11—C12—C13114.5 (4)C21—C24—H24A109.5
C11—C12—H12A108.6C21—C24—H24B109.5
C13—C12—H12A108.6H24A—C24—H24B109.5
C11—C12—H12B108.6C21—C24—H24C109.5
C13—C12—H12B108.6H24A—C24—H24C109.5
H12A—C12—H12B107.6H24B—C24—H24C109.5
C1—C4—C5—C1047.4 (8)O3—N—C14—C13110.0 (5)
C3—C4—C5—C1079.0 (8)O2—N—C14—C1366.9 (6)
C2—C4—C5—C10164.1 (6)C15—C13—C14—N79.7 (5)
C1—C4—C5—C6131.4 (6)C12—C13—C14—N49.5 (5)
C3—C4—C5—C6102.2 (8)C14—C13—C15—C1698.0 (5)
C2—C4—C5—C614.8 (8)C12—C13—C15—C1631.1 (6)
C10—C5—C6—C72.6 (7)C14—C13—C15—C2085.2 (6)
C4—C5—C6—C7176.3 (5)C12—C13—C15—C20145.7 (5)
C5—C6—C7—C80.8 (7)C20—C15—C16—C170.7 (7)
C6—C7—C8—C91.8 (6)C13—C15—C16—C17177.6 (4)
C6—C7—C8—C11175.8 (4)C15—C16—C17—C181.2 (8)
C7—C8—C9—C102.4 (7)C16—C17—C18—C192.8 (7)
C11—C8—C9—C10175.2 (5)C16—C17—C18—C21179.3 (5)
C8—C9—C10—C50.6 (8)C17—C18—C19—C204.1 (8)
C6—C5—C10—C91.9 (8)C21—C18—C19—C20178.0 (5)
C4—C5—C10—C9177.0 (6)C18—C19—C20—C154.0 (9)
C9—C8—C11—O116.6 (6)C16—C15—C20—C192.1 (8)
C7—C8—C11—O1165.9 (4)C13—C15—C20—C19179.1 (5)
C9—C8—C11—C12163.8 (4)C17—C18—C21—C2319.4 (8)
C7—C8—C11—C1213.7 (6)C19—C18—C21—C23162.8 (6)
O1—C11—C12—C130.1 (6)C17—C18—C21—C24137.1 (6)
C8—C11—C12—C13179.5 (4)C19—C18—C21—C2445.2 (8)
C11—C12—C13—C15162.8 (4)C17—C18—C21—C22101.6 (7)
C11—C12—C13—C1468.1 (5)C19—C18—C21—C2276.2 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O1i0.972.523.072 (5)116
Symmetry code: (i) x+1, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC24H31NO3
Mr381.50
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)293
a, b, c (Å)20.440 (4), 17.500 (4), 6.1630 (12)
V3)2204.5 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.985, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
8662, 2247, 1527
Rint0.096
(sin θ/λ)max1)0.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.181, 1.00
No. of reflections2247
No. of parameters247
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.32

Computer programs: CAD-4 Software (Enraf-Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O1i0.972.523.072 (5)116
Symmetry code: (i) x+1, y+1, z+1/2.
 

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 (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.  Google Scholar
First citationGorman, A., Killoran, J., Oshea, C., Kenna, T., Gallagher, W. M. & Oshea, D. F. (2004). J. Am. Chem. Soc. 126, 10619–10631.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHall, M. J., McDonnell, S. O., Killoran, J. & Oshea, D. F. (2005). J. Org. Chem. 70, 5571–5578.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationLiang, Y. J., Dong, D. W., Lu, Y. M., Wang, Y., Pan, W., Chai, Y. Y. & Liu, Q. (2006). Synthesis, 19, 3301–3304.  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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds