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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3389
https://doi.org/10.1107/S1600536811048732

6′,7′-Dimeth­­oxy-1′,2′-di­hydro­spiro­[cyclo­hexane-1,2′-quinazolin]-4′(3′H)-one

Li-Jun Zhang,a* Yang Song,a Xiang-Ning Luoa and Hui Lia

aSchool of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, People's Republic of China
*Correspondence e-mail: cdlijun2002@tjut.edu.cn

(Received 27 October 2011; accepted 16 November 2011; online 23 November 2011)

In the title compound, C15H20N2O3, prepared from the reaction of 2-amino-4,5-dimeth­oxy­benzonitrile and cyclo­hexa­none, the six-membered diaza ring assumes an envelope conformation. In the crystal, inversion dimers are formed by pairs of N—H⋯O hydrogen bonds. Futher N—H⋯O hydrogen bonds link the dimers into a two-dimensional structure parallel to (001).

Related literature

For further information on the title compound, see: Chen et al. (2007[Chen, K., Al Aowad, A. F., Adelstein, S. J. & Kassis, A. I. (2007). J. Med. Chem. 50, 663-673.]). For related structures, see: Zhang et al. (2008[Zhang, L., Li, J., Shi, D. & Chen, J. (2008). Acta Cryst. E64, o449.]). For the biological activity of related compounds, see: Hour et al. (2000[Hour, M., Huang, L., Kuo, S., Xia, Y., Bastow, K., Nakanishi, Y., Hamel, E. & Lee, K. (2000). J. Med. Chem. 43, 4479-4487.]).

[Scheme 1]

Experimental

Crystal data

  • C15H20N2O3

  • Mr = 276.33

  • Monoclinic, P 21 /c

  • a = 11.667 (2) Å

  • b = 9.6376 (19) Å

  • c = 12.307 (3) Å

  • β = 101.02 (3)°

  • V = 1358.3 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 113 K

  • 0.14 × 0.12 × 0.10 mm
Data collection

  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2004[Rigaku (2004). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.987, Tmax = 0.991

  • 16366 measured reflections

  • 3224 independent reflections

  • 2759 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.100

  • S = 1.09

  • 3224 reflections

  • 192 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O3i 0.90 (1) 1.98 (1) 2.8801 (13) 176 (1)
N1—H1⋯O2ii 0.90 (1) 2.35 (1) 3.2267 (14) 168 (1)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrystalClear (Rigaku, 2004[Rigaku (2004). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811048732/bg2428sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048732/bg2428Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048732/bg2428Isup4.cdx

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048732/bg2428Isup4.cml

checkCIF report


Comment top

Dihydroquinazolin-4(3H)-ones possess a broad spectrum of biological and pharmaceutical activities, such as analgesic, antitumor, anticancer, diuretic, and herbicide activities (Hour et al., 2000). 6,7-dimethoxyl-2,2-pentamethylene-1,2-dihydroquinazolin-4(3H)-one (I), a derivative of the most useful 1,2-dihydroquinazolinones (Chen et al., 2007) was synthesized directly from the raction of 2-amino-4,5-dimethoxybenzonitrile and cyclohexanone. In order to further confirm its structure and illuminate the correlation of structural features with its biological activity, the single-crystal of title compound was determined by X-ray crystallographic analysis.

The molecular structure of (I) is shown in Fig.1. The six membered diaza ring assumes an envelope conformation. An H-bonded dimeric unit is formed around an inversion centre, through a N-H···O H-bond (Table 1, first entry); a second H-bond of the same type (Table 1, second entry) links dimers into a two-dimensional structure parallel to (001) (Fig 2).

Related literature top

For further information on the title compound, see: Chen et al. (2007). For related structures, see: Zhang et al. (2008). For the biological activity of related compounds, see: Hour et al. (2000).

Experimental top

The title compound was prepared from the reaction of 2-amino-4,5-methoxybenzonitrile (1 mmol) with cyclopentanone 1 mL in the catalysis of sodium ethoxide (0.2 mmol) at room temperature for 1 h. Then the product was precipitated spontaneously and separated by filtration. The pure desired compound I was recrystallized from ethanol in 91% yield.

Single crystals were obtained from a solution of ethanol by slow evaporation at room temperature.

Refinement top

Imino H atoms were located in a difference Fourier map and refined isotropically. Other H atoms were placed in calculated positiosn with C—H = 0.95 (aromatic ) or 0.98 Å (methylene), and refined in riding mode with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) (for methylene group).

Structure description top

Dihydroquinazolin-4(3H)-ones possess a broad spectrum of biological and pharmaceutical activities, such as analgesic, antitumor, anticancer, diuretic, and herbicide activities (Hour et al., 2000). 6,7-dimethoxyl-2,2-pentamethylene-1,2-dihydroquinazolin-4(3H)-one (I), a derivative of the most useful 1,2-dihydroquinazolinones (Chen et al., 2007) was synthesized directly from the raction of 2-amino-4,5-dimethoxybenzonitrile and cyclohexanone. In order to further confirm its structure and illuminate the correlation of structural features with its biological activity, the single-crystal of title compound was determined by X-ray crystallographic analysis.

The molecular structure of (I) is shown in Fig.1. The six membered diaza ring assumes an envelope conformation. An H-bonded dimeric unit is formed around an inversion centre, through a N-H···O H-bond (Table 1, first entry); a second H-bond of the same type (Table 1, second entry) links dimers into a two-dimensional structure parallel to (001) (Fig 2).

For further information on the title compound, see: Chen et al. (2007). For related structures, see: Zhang et al. (2008). For the biological activity of related compounds, see: Hour et al. (2000).

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); 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 (I), (Displacement ellipsoids drawn at a 50% probability level).
[Figure 2] Fig. 2. Packing diagram of (I), showing one dimer and the way they connect into (001) layers (H bonds in dashed lines).
6',7'-Dimethoxy-1',2'-dihydrospiro[cyclohexane-1,2'-quinazoline]- 4'(3'H)-one top
Crystal data top
C15H20N2O3F(000) = 592
Mr = 276.33Dx = 1.351 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3746 reflections
a = 11.667 (2) Åθ = 1.8–27.9°
b = 9.6376 (19) ŵ = 0.10 mm−1
c = 12.307 (3) ÅT = 113 K
β = 101.02 (3)°Prism, colourless
V = 1358.3 (5) Å30.14 × 0.12 × 0.10 mm
Z = 4
Data collection top
Rigaku Saturn
diffractometer		3224 independent reflections
Radiation source: rotating anode2759 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.031
ω scansθmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2004)		h = −15→14
Tmin = 0.987, Tmax = 0.991k = −12→12
16366 measured reflectionsl = −16→16
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)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0565P)2 + 0.1742P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
3224 reflectionsΔρmax = 0.33 e Å−3
192 parametersΔρmin = −0.18 e Å−3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.073 (6)
Crystal data top
C15H20N2O3V = 1358.3 (5) Å3
Mr = 276.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.667 (2) ŵ = 0.10 mm−1
b = 9.6376 (19) ÅT = 113 K
c = 12.307 (3) Å0.14 × 0.12 × 0.10 mm
β = 101.02 (3)°
Data collection top
Rigaku Saturn
diffractometer		3224 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2004)		2759 reflections with I > 2σ(I)
Tmin = 0.987, Tmax = 0.991Rint = 0.031
16366 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0362 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.33 e Å−3
3224 reflectionsΔρmin = −0.18 e Å−3
192 parameters
Special details top

Experimental. Mp. 251–252°C. IR (KBr, cm-1): 3290, 3220, 2930, 2838, 1651, 1619, 1507; 1H NMR (400 MHz, DMSO-d6) δH: 1.23–1.78 (10H, m, C5H10), 3.66(3H, s, OCH3), 3.74(3H, s, OCH3), 6.34 (1H, s, NH), 6.54 (1H, s, ArH), 7.07 (1H, s, ArH), 7.68 (1H, s, NH); 13 C NMR (100 MHz, DMSO-d6) δC: 21.1 (2 C), 24.8, 37.0 (2 C), 55.4, 56.0, 68.2, 99.2, 106.0, 110.0, 141.1, 142.6, 153.9, 163.4; MS (ESI): m/z (%) = 277.2 (100) [M+H]+; Anal. Calcd. for C15H20N2O3: C 65.20, H 7.30, N 10.14; found C 64.98, H 7.80, N 9.52.

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
O1−0.16045 (6)0.43728 (8)0.80668 (6)0.0203 (2)
O2−0.06468 (6)0.26156 (8)0.95294 (6)0.0205 (2)
O30.37247 (6)0.40011 (8)1.03202 (6)0.0200 (2)
N10.21715 (7)0.61646 (9)0.76365 (7)0.0153 (2)
N20.38438 (7)0.54041 (10)0.88635 (7)0.0158 (2)
C10.14797 (9)0.52723 (11)0.81032 (8)0.0134 (2)
C20.02567 (9)0.52808 (11)0.77773 (8)0.0145 (2)
H2A−0.00990.58710.72150.017*
C3−0.04157 (9)0.44150 (11)0.82915 (8)0.0151 (2)
C40.01161 (9)0.34735 (11)0.91200 (8)0.0152 (2)
C50.13085 (9)0.34881 (11)0.94579 (8)0.0153 (2)
H50.16600.28941.00200.018*
C60.20027 (9)0.43927 (11)0.89624 (8)0.0142 (2)
C7−0.22059 (9)0.54426 (13)0.73899 (10)0.0226 (3)
H7A−0.19170.63300.76730.034*
H7B−0.30260.53820.73940.034*
H7C−0.20800.53370.66460.034*
C8−0.01742 (10)0.18413 (12)1.04951 (9)0.0199 (2)
H8A0.03750.11751.03210.030*
H8B−0.07930.13681.07560.030*
H8C0.02140.24591.10590.030*
C90.32557 (9)0.45515 (11)0.94320 (8)0.0152 (2)
C100.33946 (9)0.57909 (11)0.77095 (8)0.0134 (2)
C110.40780 (9)0.70426 (11)0.74216 (8)0.0152 (2)
H11A0.49070.68430.76210.018*
H11B0.39160.78310.78590.018*
C120.37805 (9)0.74296 (11)0.61959 (9)0.0170 (2)
H12A0.29790.77510.60150.020*
H12B0.42830.81820.60510.020*
C130.39356 (10)0.61926 (13)0.54656 (9)0.0222 (3)
H13A0.47560.59460.55800.027*
H13B0.36850.64480.46940.027*
C140.32319 (10)0.49419 (12)0.57250 (9)0.0207 (3)
H14A0.24050.51530.55320.025*
H14B0.33870.41560.52820.025*
C150.35496 (9)0.45662 (11)0.69493 (9)0.0164 (2)
H15A0.43560.42580.71180.020*
H15B0.30620.38010.70980.020*
H10.1830 (11)0.6677 (13)0.7058 (9)0.029 (4)*
H20.4604 (8)0.5564 (14)0.9151 (11)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0111 (4)0.0221 (4)0.0265 (4)−0.0010 (3)0.0004 (3)0.0047 (3)
O20.0161 (4)0.0231 (4)0.0215 (4)−0.0058 (3)0.0013 (3)0.0065 (3)
O30.0163 (4)0.0240 (4)0.0179 (4)−0.0021 (3)−0.0015 (3)0.0081 (3)
N10.0115 (4)0.0175 (5)0.0169 (4)0.0020 (3)0.0028 (3)0.0055 (4)
N20.0115 (4)0.0201 (5)0.0145 (4)−0.0026 (4)−0.0007 (3)0.0032 (4)
C10.0146 (5)0.0130 (5)0.0130 (5)−0.0005 (4)0.0036 (4)−0.0014 (4)
C20.0158 (5)0.0141 (5)0.0129 (5)0.0015 (4)0.0015 (4)0.0000 (4)
C30.0116 (5)0.0165 (5)0.0163 (5)−0.0009 (4)0.0007 (4)−0.0036 (4)
C40.0162 (5)0.0141 (5)0.0158 (5)−0.0035 (4)0.0041 (4)−0.0013 (4)
C50.0171 (5)0.0147 (5)0.0136 (5)−0.0001 (4)0.0016 (4)0.0011 (4)
C60.0131 (5)0.0147 (5)0.0141 (5)−0.0003 (4)0.0013 (4)−0.0005 (4)
C70.0140 (5)0.0258 (6)0.0260 (6)0.0026 (4)−0.0012 (4)0.0029 (5)
C80.0219 (6)0.0187 (5)0.0185 (5)−0.0053 (4)0.0029 (4)0.0029 (4)
C90.0149 (5)0.0148 (5)0.0157 (5)−0.0007 (4)0.0019 (4)0.0003 (4)
C100.0108 (5)0.0156 (5)0.0134 (5)0.0002 (4)0.0011 (4)0.0024 (4)
C110.0139 (5)0.0152 (5)0.0167 (5)−0.0022 (4)0.0030 (4)0.0003 (4)
C120.0173 (5)0.0172 (5)0.0172 (5)−0.0012 (4)0.0047 (4)0.0029 (4)
C130.0266 (6)0.0246 (6)0.0173 (5)−0.0009 (5)0.0089 (5)0.0000 (4)
C140.0243 (6)0.0207 (6)0.0173 (5)−0.0013 (5)0.0049 (4)−0.0036 (4)
C150.0162 (5)0.0138 (5)0.0195 (5)0.0009 (4)0.0038 (4)0.0002 (4)
Geometric parameters (Å, º) top
O1—C31.3619 (12)C7—H7B0.9600
O1—C71.4233 (13)C7—H7C0.9600
O2—C41.3789 (12)C8—H8A0.9600
O2—C81.4223 (13)C8—H8B0.9600
O3—C91.2438 (13)C8—H8C0.9600
N1—C11.3777 (13)C10—C111.5246 (14)
N1—C101.4577 (13)C10—C151.5381 (14)
N1—H10.895 (8)C11—C121.5280 (14)
N2—C91.3487 (14)C11—H11A0.9700
N2—C101.4650 (13)C11—H11B0.9700
N2—H20.903 (9)C12—C131.5246 (16)
C1—C61.4009 (14)C12—H12A0.9700
C1—C21.4064 (14)C12—H12B0.9700
C2—C31.3791 (15)C13—C141.5261 (16)
C2—H2A0.9300C13—H13A0.9700
C3—C41.4164 (15)C13—H13B0.9700
C4—C51.3737 (15)C14—C151.5250 (15)
C5—C61.4060 (14)C14—H14A0.9700
C5—H50.9300C14—H14B0.9700
C6—C91.4735 (14)C15—H15A0.9700
C7—H7A0.9600C15—H15B0.9700
C3—O1—C7117.79 (9)O3—C9—C6122.49 (10)
C4—O2—C8116.47 (8)N2—C9—C6115.13 (9)
C1—N1—C10117.69 (8)N1—C10—N2106.68 (8)
C1—N1—H1118.0 (9)N1—C10—C11109.84 (8)
C10—N1—H1117.8 (9)N2—C10—C11108.70 (8)
C9—N2—C10122.33 (9)N1—C10—C15112.31 (9)
C9—N2—H2117.4 (9)N2—C10—C15109.43 (8)
C10—N2—H2118.6 (9)C11—C10—C15109.77 (8)
N1—C1—C6119.15 (9)C10—C11—C12113.10 (8)
N1—C1—C2121.38 (9)C10—C11—H11A109.0
C6—C1—C2119.37 (9)C12—C11—H11A109.0
C3—C2—C1120.05 (10)C10—C11—H11B109.0
C3—C2—H2A120.0C12—C11—H11B109.0
C1—C2—H2A120.0H11A—C11—H11B107.8
O1—C3—C2124.84 (10)C13—C12—C11111.16 (9)
O1—C3—C4114.59 (9)C13—C12—H12A109.4
C2—C3—C4120.57 (9)C11—C12—H12A109.4
C5—C4—O2125.64 (9)C13—C12—H12B109.4
C5—C4—C3119.36 (10)C11—C12—H12B109.4
O2—C4—C3115.00 (9)H12A—C12—H12B108.0
C4—C5—C6120.60 (10)C12—C13—C14111.41 (9)
C4—C5—H5119.7C12—C13—H13A109.3
C6—C5—H5119.7C14—C13—H13A109.3
C1—C6—C5119.92 (9)C12—C13—H13B109.3
C1—C6—C9119.31 (9)C14—C13—H13B109.3
C5—C6—C9120.32 (9)H13A—C13—H13B108.0
O1—C7—H7A109.5C15—C14—C13110.82 (9)
O1—C7—H7B109.5C15—C14—H14A109.5
H7A—C7—H7B109.5C13—C14—H14A109.5
O1—C7—H7C109.5C15—C14—H14B109.5
H7A—C7—H7C109.5C13—C14—H14B109.5
H7B—C7—H7C109.5H14A—C14—H14B108.1
O2—C8—H8A109.5C14—C15—C10112.59 (9)
O2—C8—H8B109.5C14—C15—H15A109.1
H8A—C8—H8B109.5C10—C15—H15A109.1
O2—C8—H8C109.5C14—C15—H15B109.1
H8A—C8—H8C109.5C10—C15—H15B109.1
H8B—C8—H8C109.5H15A—C15—H15B107.8
O3—C9—N2122.27 (9)
C10—N1—C1—C624.75 (14)C10—N2—C9—O3165.20 (10)
C10—N1—C1—C2−158.81 (9)C10—N2—C9—C6−18.58 (14)
N1—C1—C2—C3−177.33 (9)C1—C6—C9—O3165.95 (10)
C6—C1—C2—C3−0.90 (15)C5—C6—C9—O3−6.30 (16)
C7—O1—C3—C2−10.82 (15)C1—C6—C9—N2−10.26 (14)
C7—O1—C3—C4169.32 (9)C5—C6—C9—N2177.49 (9)
C1—C2—C3—O1177.71 (9)C1—N1—C10—N2−48.06 (12)
C1—C2—C3—C4−2.43 (15)C1—N1—C10—C11−165.70 (9)
C8—O2—C4—C510.36 (15)C1—N1—C10—C1571.83 (11)
C8—O2—C4—C3−168.79 (9)C9—N2—C10—N146.21 (13)
O1—C3—C4—C5−176.12 (9)C9—N2—C10—C11164.60 (9)
C2—C3—C4—C54.01 (15)C9—N2—C10—C15−75.52 (12)
O1—C3—C4—O23.09 (13)N1—C10—C11—C12−70.47 (11)
C2—C3—C4—O2−176.78 (9)N2—C10—C11—C12173.15 (8)
O2—C4—C5—C6178.66 (9)C15—C10—C11—C1253.49 (11)
C3—C4—C5—C6−2.21 (15)C10—C11—C12—C13−54.58 (12)
N1—C1—C6—C5179.18 (9)C11—C12—C13—C1454.73 (12)
C2—C1—C6—C52.67 (15)C12—C13—C14—C15−55.51 (12)
N1—C1—C6—C96.90 (14)C13—C14—C15—C1055.82 (12)
C2—C1—C6—C9−169.61 (9)N1—C10—C15—C1468.32 (11)
C4—C5—C6—C1−1.10 (15)N2—C10—C15—C14−173.39 (8)
C4—C5—C6—C9171.11 (9)C11—C10—C15—C14−54.19 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.90 (1)1.98 (1)2.8801 (13)176 (1)
N1—H1···O2ii0.90 (1)2.35 (1)3.2267 (14)168 (1)
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC15H20N2O3
Mr276.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)11.667 (2), 9.6376 (19), 12.307 (3)
β (°) 101.02 (3)
V (Å3)1358.3 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.14 × 0.12 × 0.10
Data collection
DiffractometerRigaku Saturn
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2004)
Tmin, Tmax0.987, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections		16366, 3224, 2759
Rint0.031
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.100, 1.09
No. of reflections3224
No. of parameters192
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.33, −0.18

Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.903 (9)1.979 (9)2.8801 (13)175.7 (13)
N1—H1···O2ii0.895 (8)2.347 (9)3.2267 (14)167.5 (12)
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, y+1/2, −z+3/2.
 

Acknowledgements

We thank the Tianjin Municipal Commission of Education for its financial support (SB 20080060) and Professor Haibin Song of Naikai University for the X-ray diffraction analysis.

References

First citationChen, K., Al Aowad, A. F., Adelstein, S. J. & Kassis, A. I. (2007). J. Med. Chem. 50, 663–673.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationHour, M., Huang, L., Kuo, S., Xia, Y., Bastow, K., Nakanishi, Y., Hamel, E. & Lee, K. (2000). J. Med. Chem. 43, 4479–4487.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationRigaku (2004). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZhang, L., Li, J., Shi, D. & Chen, J. (2008). Acta Cryst. E64, o449.  Web of Science CSD CrossRef 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.

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3389
https://doi.org/10.1107/S1600536811048732
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