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ISSN: 2056-9890

(S)-1-[3,5-Bis­(tri­fluoro­meth­yl)phen­yl]-N-methylethyl­amine–(R)-2-hy­droxy­butane­dioic acid (1/1)

aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing, People's Republic of China
*Correspondence e-mail: zhuhaibin@seu.edu.cn

(Received 8 December 2008; accepted 18 December 2008; online 24 December 2008)

In the title compound, C11H11F6N·C4H6O5, a key inter­mediate in the synthesis of the NK1 receptor antagonist of casopitant, the F atoms of the trifluoro­methyl groups are disordered over two sites with equal occupancies. In the crystal, the components are linked by bifurcated N—H⋯(O,O) hydrogen bonds.

Related literature

The title compound is a key intermediate for the synthesis of casopitant, which is an NK1 receptor antagonist (Humphrey, 2003[Humphrey, J. M. (2003). Curr. Topics Med. Chem. 3, 1423-1435.]) for the treatment of chemotheraphy-induced nausea and vomiting (CINV) (Lohr, 2008[Lohr, L. (2008). Cancer J. 14, 85-93.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11F6N·C4H6O5

  • Mr = 405.30

  • Monoclinic, P 21

  • a = 6.6770 (13) Å

  • b = 8.4510 (17) Å

  • c = 16.366 (3) Å

  • β = 100.05 (3)°

  • V = 909.3 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.15 mm−1

  • T = 298 (2) K

  • 0.30 × 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 = 0.957, Tmax = 0.985

  • 1915 measured reflections

  • 1757 independent reflections

  • 1067 reflections with I > 2σ(I)

  • Rint = 0.058

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

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.154

  • S = 1.00

  • 1757 reflections

  • 220 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N—H0A⋯O4i 0.86 2.37 2.914 (7) 122
N—H0A⋯O3ii 0.86 2.20 2.887 (7) 137
Symmetry codes: (i) x-1, y, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+1].

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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound, C11H11F6N.C4H6O5, is a key intermediate for the synthesis of casopitant, which is an NK1 receptor antagonist (Humphrey, 2003) for the treatment of chemotheraphy-induced nausea and vomiting (CINV) (Lohr, 2008).

The molecular structure of the title compound is shown in Fig.1. The F atoms of the trifluoromethyl group are disordered over two sites in a 0.50:0.50 ratio. N—H···O hydrogen bonding interactions occur between (S)-1-(3, 5-bis(trifluoromethyl)-phenyl)ethylamine N-monomethyl and (R)-2-hydroxybutanedioic acid (Table 1).

Related literature top

For the NK1 receptor antagonist, see: Humphrey (2003).

Experimental top

To a solution of 3, 5-bis(trifluoromethyl)-phenyl)ethylamine N-monomethyl (2.71 g, 10 mmol) in EtOAc (25 ml), (R)-2-hydroxybutanedioic acid (1.34,10 mmol) was added portionwise. The suspension was stirred for 2h at 298 K, then for 3 h at 273 K. The suspension was filtered and the cake was washed with EtOAc (20 ml). The solid was dried under vacucum obtaining the crude title compound (1.48 g). Single crystal of the title compound suitable for X-ray diffraction was obtained by slow evaporation of the EtOAc solution of the title compound.

Refinement top

All H atoms were positoned geometrically and allowed to ride on their parent atoms, with C—H = 0.93Å for aromatic H atoms, 0.96Å for methyl H atoms, 0.97Å for methylene H atoms, 0.98Å for methine H atoms and O—H = 0.82 Å, N—H = 0.86 Å, respectively. [Uiso (H) = 1.2Ueq(C) for aromatic, methylene and methine; Uiso(H) = 1.5 Ueq(C) for methyl, Uiso(H) = 1.2Ueq(N); Uiso(H) = 1.5 Ueq(O).]

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius,1989); cell refinement: CAD-4 Software; 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, drawn with 30% probability ellipsoids.
(S)-1-[3,5-Bis(trifluoromethyl)phenyl]-N-methylethylamine– (R)-2-hydroxybutanedioic acid (1/1) top
Crystal data top
C11H11F6N·C4H6O5F(000) = 416
Mr = 405.30Dx = 1.480 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 6.6770 (13) Åθ = 9–12°
b = 8.4510 (17) ŵ = 0.15 mm1
c = 16.366 (3) ÅT = 298 K
β = 100.05 (3)°Needle, colourless
V = 909.3 (3) Å30.30 × 0.10 × 0.10 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
1067 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 25.3°, θmin = 1.3°
ω/2θ scansh = 07
Absorption correction: ψ scan
(North et al., 1968)
k = 010
Tmin = 0.957, Tmax = 0.985l = 1919
1915 measured reflections3 standard reflections every 200 reflections
1757 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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.060P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
1757 reflections(Δ/σ)max < 0.001
220 parametersΔρmax = 0.18 e Å3
2 restraintsΔρmin = 0.27 e Å3
Crystal data top
C11H11F6N·C4H6O5V = 909.3 (3) Å3
Mr = 405.30Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.6770 (13) ŵ = 0.15 mm1
b = 8.4510 (17) ÅT = 298 K
c = 16.366 (3) Å0.30 × 0.10 × 0.10 mm
β = 100.05 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1067 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.058
Tmin = 0.957, Tmax = 0.9853 standard reflections every 200 reflections
1915 measured reflections intensity decay: 1%
1757 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0632 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.00Δρmax = 0.18 e Å3
1757 reflectionsΔρmin = 0.27 e Å3
220 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*/UeqOcc. (<1)
F10.9058 (17)0.4852 (16)0.9973 (8)0.1120.50
F30.9270 (13)0.6270 (13)0.8772 (6)0.0830.50
F21.0892 (15)0.4013 (14)0.9084 (6)0.1010.50
F1'0.7985 (16)0.6070 (16)0.9651 (7)0.1110.50
F2'1.000 (2)0.4376 (16)0.9758 (7)0.1110.50
F3'0.9991 (17)0.5461 (16)0.8769 (7)0.1150.50
F40.5055 (13)0.0158 (14)0.9651 (7)0.0850.50
F50.3781 (15)0.0926 (12)0.8429 (6)0.0800.50
F60.6975 (13)0.0918 (12)0.8664 (6)0.0780.50
F4'0.5831 (15)0.0443 (15)0.9665 (8)0.0970.50
F5'0.3083 (15)0.0556 (14)0.8707 (6)0.0950.50
F6'0.6174 (16)0.1374 (14)0.8609 (7)0.0930.50
N0.3387 (7)0.3503 (6)0.6045 (3)0.0464 (12)
H0A0.25340.28880.57440.056*
C10.8859 (12)0.4933 (11)0.9164 (5)0.081
C20.5244 (14)0.0104 (14)0.8816 (5)0.094 (3)
C30.5326 (11)0.1454 (10)0.8548 (4)0.063 (2)
C40.4157 (10)0.2037 (8)0.7869 (4)0.0543 (17)
H4A0.31360.14080.75740.065*
C50.4445 (9)0.3611 (9)0.7587 (4)0.0527 (16)
C60.5931 (11)0.4465 (10)0.8000 (4)0.072 (2)
H6A0.61370.54880.78210.087*
C70.7249 (13)0.3856 (12)0.8723 (5)0.080 (2)
C80.6962 (12)0.2426 (12)0.8978 (5)0.079 (3)
H8A0.78170.20260.94410.095*
C90.3017 (8)0.4239 (8)0.6855 (3)0.0482 (15)
H9A0.32740.53770.68230.058*
C100.0783 (9)0.4033 (9)0.6903 (4)0.0646 (19)
H10A0.05070.45080.74050.097*
H10B0.04610.29260.69020.097*
H10C0.00330.45350.64330.097*
C110.5373 (9)0.3961 (9)0.5832 (4)0.0606 (18)
H11A0.55420.34550.53230.091*
H11B0.64470.36360.62690.091*
H11C0.54190.50880.57660.091*
O10.6777 (8)0.0742 (7)0.6474 (4)0.0869 (18)
O20.5220 (7)0.1471 (5)0.6689 (3)0.0652 (13)
H2A0.42260.09120.65260.098*
O30.8263 (6)0.2740 (5)0.5576 (3)0.0579 (12)
H3A0.88250.34370.53510.087*
O41.1965 (6)0.0264 (5)0.6157 (3)0.0540 (11)
O50.9516 (7)0.0076 (6)0.5086 (3)0.0678 (15)
H5A1.01840.07430.48880.102*
C120.6858 (11)0.0671 (9)0.6676 (4)0.0551 (17)
C130.8797 (9)0.1508 (8)0.6891 (4)0.0522 (15)
H13A0.85870.24810.71790.063*
H13B0.97440.08570.72650.063*
C140.9715 (8)0.1898 (7)0.6122 (3)0.0428 (14)
H14A1.08940.25880.62920.051*
C151.0461 (9)0.0360 (7)0.5766 (4)0.0464 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1120.1120.1120.0000.0200.000
F30.0830.0830.0830.0000.0150.000
F20.1010.1010.1010.0000.0180.000
F1'0.1110.1110.1110.0000.0190.000
F2'0.1110.1110.1110.0000.0190.000
F3'0.1150.1150.1150.0000.0200.000
F40.0850.0850.0850.0000.0150.000
F50.0800.0800.0800.0000.0140.000
F60.0780.0780.0780.0000.0140.000
F4'0.0970.0970.0970.0000.0170.000
F5'0.0950.0950.0950.0000.0170.000
F6'0.0930.0930.0930.0000.0160.000
N0.050 (3)0.044 (3)0.047 (3)0.015 (3)0.010 (2)0.004 (3)
C10.0720.1000.0670.0330.0030.033
C20.097 (7)0.114 (8)0.069 (6)0.014 (7)0.012 (5)0.000 (6)
C30.063 (4)0.065 (5)0.059 (4)0.016 (4)0.005 (4)0.000 (4)
C40.055 (4)0.058 (4)0.048 (3)0.002 (4)0.002 (3)0.002 (3)
C50.053 (4)0.065 (5)0.042 (3)0.004 (4)0.013 (3)0.002 (3)
C60.075 (5)0.084 (6)0.055 (4)0.014 (5)0.003 (4)0.012 (4)
C70.068 (5)0.076 (6)0.089 (6)0.003 (5)0.006 (4)0.001 (5)
C80.068 (5)0.102 (7)0.061 (5)0.000 (5)0.007 (4)0.014 (5)
C90.053 (3)0.045 (3)0.045 (3)0.009 (3)0.003 (3)0.007 (3)
C100.054 (4)0.069 (5)0.073 (4)0.005 (4)0.017 (3)0.014 (4)
C110.047 (3)0.062 (4)0.072 (4)0.015 (3)0.010 (3)0.003 (4)
O10.081 (4)0.067 (4)0.120 (5)0.011 (3)0.037 (3)0.010 (4)
O20.068 (3)0.053 (3)0.074 (3)0.002 (3)0.009 (2)0.002 (3)
O30.059 (3)0.043 (2)0.074 (3)0.012 (2)0.018 (2)0.011 (2)
O40.046 (2)0.053 (3)0.062 (3)0.011 (2)0.009 (2)0.002 (2)
O50.082 (3)0.066 (3)0.052 (2)0.022 (3)0.003 (2)0.015 (3)
C120.062 (4)0.061 (4)0.046 (4)0.003 (4)0.022 (3)0.005 (3)
C130.060 (4)0.051 (4)0.048 (3)0.005 (4)0.016 (3)0.003 (3)
C140.041 (3)0.048 (4)0.042 (3)0.007 (3)0.014 (3)0.006 (3)
C150.046 (3)0.036 (3)0.061 (4)0.005 (3)0.020 (3)0.004 (3)
Geometric parameters (Å, º) top
F1—C11.309 (14)C7—C81.304 (13)
F3—C11.352 (13)C8—H8A0.9300
F2—C11.589 (14)C9—C101.517 (8)
F1'—C11.436 (13)C9—H9A0.9800
F2'—C11.219 (13)C10—H10A0.9600
F3'—C11.167 (12)C10—H10B0.9600
F4—C21.395 (13)C10—H10C0.9600
F5—C21.274 (12)C11—H11A0.9600
F6—C21.404 (11)C11—H11B0.9600
F4'—C21.405 (14)C11—H11C0.9600
F5'—C21.474 (13)O1—C121.237 (9)
F6'—C21.313 (15)O2—C121.290 (8)
N—C111.480 (7)O2—H2A0.8200
N—C91.523 (7)O3—C141.394 (7)
N—H0A0.8600O3—H3A0.8200
C1—C71.495 (11)O4—C151.213 (7)
C2—C31.392 (13)O5—C151.236 (7)
C3—C41.336 (9)O5—H5A0.8200
C3—C81.447 (11)C12—C131.463 (9)
C4—C51.432 (10)C13—C141.530 (8)
C4—H4A0.9300C13—H13A0.9700
C5—C61.315 (9)C13—H13B0.9700
C5—C91.492 (8)C14—C151.543 (8)
C6—C71.441 (10)C14—H14A0.9800
C6—H6A0.9300
C11—N—C9112.7 (5)C5—C6—C7121.6 (8)
C11—N—H0A123.6C5—C6—H6A119.2
C9—N—H0A123.6C7—C6—H6A119.2
F3'—C1—F2'102.5 (11)C8—C7—C6119.4 (8)
F3'—C1—F1128.3 (11)C8—C7—C1122.9 (8)
F2'—C1—F3123.5 (10)C6—C7—C1117.6 (8)
F1—C1—F3122.1 (10)C7—C8—C3120.8 (8)
F3'—C1—F1'114.7 (11)C7—C8—H8A119.6
F2'—C1—F1'94.2 (9)C3—C8—H8A119.6
F1—C1—F1'56.8 (8)C5—C9—C10114.4 (5)
F3—C1—F1'80.8 (8)C5—C9—N112.1 (5)
F3'—C1—C7116.5 (10)C10—C9—N108.0 (5)
F2'—C1—C7116.5 (9)C5—C9—H9A107.3
F1—C1—C7113.2 (9)C10—C9—H9A107.3
F3—C1—C7117.9 (7)N—C9—H9A107.3
F1'—C1—C7110.3 (8)C9—C10—H10A109.5
F3'—C1—F259.7 (8)C9—C10—H10B109.5
F2'—C1—F256.9 (8)H10A—C10—H10B109.5
F1—C1—F296.9 (8)C9—C10—H10C109.5
F3—C1—F297.0 (8)H10A—C10—H10C109.5
F1'—C1—F2144.0 (8)H10B—C10—H10C109.5
C7—C1—F2102.4 (8)N—C11—H11A109.5
F5—C2—F6'77.4 (9)N—C11—H11B109.5
F5—C2—C3115.3 (9)H11A—C11—H11B109.5
F6'—C2—C3130.1 (9)N—C11—H11C109.5
F5—C2—F4106.1 (10)H11A—C11—H11C109.5
F6'—C2—F4110.7 (10)H11B—C11—H11C109.5
C3—C2—F4110.8 (10)C12—O2—H2A109.5
F5—C2—F6103.2 (10)C14—O3—H3A109.5
C3—C2—F6109.2 (9)C15—O5—H5A109.5
F4—C2—F6112.1 (8)O1—C12—O2120.8 (7)
F5—C2—F4'116.0 (10)O1—C12—C13121.8 (7)
F6'—C2—F4'91.5 (9)O2—C12—C13117.4 (7)
C3—C2—F4'119.0 (10)C12—C13—C14111.8 (5)
F6—C2—F4'88.8 (8)C12—C13—H13A109.3
F6'—C2—F5'104.7 (10)C14—C13—H13A109.3
C3—C2—F5'107.4 (9)C12—C13—H13B109.3
F4—C2—F5'81.7 (8)C14—C13—H13B109.3
F6—C2—F5'132.1 (11)H13A—C13—H13B107.9
F4'—C2—F5'99.5 (9)O3—C14—C13107.7 (4)
C4—C3—C2124.2 (8)O3—C14—C15115.0 (5)
C4—C3—C8118.5 (8)C13—C14—C15109.4 (5)
C2—C3—C8116.8 (8)O3—C14—H14A108.2
C3—C4—C5121.2 (7)C13—C14—H14A108.2
C3—C4—H4A119.4C15—C14—H14A108.2
C5—C4—H4A119.4O4—C15—O5126.3 (6)
C6—C5—C4118.4 (7)O4—C15—C14117.3 (5)
C6—C5—C9122.5 (7)O5—C15—C14116.3 (5)
C4—C5—C9119.1 (6)
F5—C2—C3—C48.6 (14)F2—C1—C7—C863.3 (12)
F6'—C2—C3—C486.2 (14)F3'—C1—C7—C656.5 (14)
F4—C2—C3—C4129.1 (9)F2'—C1—C7—C6177.7 (11)
F6—C2—C3—C4107.0 (10)F1—C1—C7—C6138.1 (10)
F4'—C2—C3—C4153.3 (8)F3—C1—C7—C613.7 (14)
F5'—C2—C3—C441.5 (11)F1'—C1—C7—C676.5 (10)
F5—C2—C3—C8179.6 (8)F2—C1—C7—C6118.7 (8)
F6'—C2—C3—C885.6 (13)C6—C7—C8—C30.6 (14)
F4—C2—C3—C859.1 (11)C1—C7—C8—C3177.4 (8)
F6—C2—C3—C864.8 (10)C4—C3—C8—C72.0 (13)
F4'—C2—C3—C834.8 (13)C2—C3—C8—C7174.3 (9)
F5'—C2—C3—C8146.6 (8)C6—C5—C9—C10128.2 (7)
C2—C3—C4—C5174.3 (8)C4—C5—C9—C1049.9 (8)
C8—C3—C4—C52.6 (11)C6—C5—C9—N108.5 (7)
C3—C4—C5—C61.8 (11)C4—C5—C9—N73.5 (7)
C3—C4—C5—C9176.3 (6)C11—N—C9—C566.8 (7)
C4—C5—C6—C70.3 (11)C11—N—C9—C10166.3 (5)
C9—C5—C6—C7177.8 (7)O1—C12—C13—C1475.2 (9)
C5—C6—C7—C80.3 (13)O2—C12—C13—C14103.5 (7)
C5—C6—C7—C1178.4 (8)C12—C13—C14—O355.0 (7)
F3'—C1—C7—C8125.5 (13)C12—C13—C14—C1570.6 (7)
F2'—C1—C7—C84.3 (17)O3—C14—C15—O4167.3 (5)
F1—C1—C7—C839.9 (15)C13—C14—C15—O471.4 (6)
F3—C1—C7—C8168.3 (10)O3—C14—C15—O59.4 (7)
F1'—C1—C7—C8101.5 (12)C13—C14—C15—O5111.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H0A···O4i0.862.372.914 (7)122
N—H0A···O3ii0.862.202.887 (7)137
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC11H11F6N·C4H6O5
Mr405.30
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)6.6770 (13), 8.4510 (17), 16.366 (3)
β (°) 100.05 (3)
V3)909.3 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.15
Crystal size (mm)0.30 × 0.10 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.957, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
1915, 1757, 1067
Rint0.058
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.154, 1.00
No. of reflections1757
No. of parameters220
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.27

Computer programs: CAD-4 Software (Enraf–Nonius,1989), CAD-4 Software, 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
N—H0A···O4i0.862.372.914 (7)121.7
N—H0A···O3ii0.862.202.887 (7)137.0
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1.
 

Acknowledgements

The authors thank the China Postdoctoral Research Fund (20070411010) and the Young Teachers' Starting Fund of Southeast University for support.

References

First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationHumphrey, J. M. (2003). Curr. Topics Med. Chem. 3, 1423–1435.  Web of Science CrossRef CAS Google Scholar
First citationLohr, L. (2008). Cancer J. 14, 85–93.  Web of Science CrossRef PubMed CAS 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

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