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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 o3348
https://doi.org/10.1107/S160053681104815X

2-[4-(2-Hy­dr­oxy­eth­­oxy)phenyl]-4,4,5,5-tetra­methyl-2-imidazoline-1-oxyl 3-oxide

Lin-Lin Jing,a Hui-Ping Ma,a Xiao-Fei Fan,a Lei Hea and Zheng-Ping Jiaa*

aDepartment of Pharmacy, Lanzhou General Hospital of PLA, Key Laboratory of the Prevention and Cure of Plateau Environmental Damage, PLA 730050, Lanzhou Gansu, People's Republic of China
*Correspondence e-mail: zhengping_jia@yahoo.cn

(Received 8 November 2011; accepted 13 November 2011; online 19 November 2011)

In the title compound, C15H21N2O4, the imidazoline ring displays a twisted conformation. The dihedral angle between the mean plane of the imidazoline ring and the benzene ring is 33.50 (12)°. In the crystal, mol­ecules are connected by O—H⋯O hydrogen bonds, forming a zigzag chain along the c axis. The chains are linked by C—H⋯O and C—H⋯π inter­actions.

Related literature

For the preparation of the title compound, see: Ullman et al. (1974[Ullman, E. F., Osiecki, J. H., Boocock, D. G. B. & Darcy, R. (1974). J. Am. Chem. Soc. 96, 7049-7053.]). For biological properties of nitronyl nitroxides, see: Soule et al. (2007[Soule, B. P., Hyodo, F., Matsumoto, K., Simone, N. L., Cook, J. A., Krishna, M. C. & Mitchell, J. B. (2007). Free Radic. Biol. Med. 42, 1632-1650.]); Blasig et al. (2002[Blasig, I. E., Mertsch, K. & Haseloff, R. F. (2002). Neuropharmacology, 43, 1006-1014.]); Qin et al. (2009[Qin, X. Y., Ding, G. R. & Sun, X. L. (2009). J. Chem. Res. pp. 511-514.]); Tanaka et al. (2007[Tanaka, K., Furuichi, K., Kozaki, M., Suzuki, S., Shiomi, D., Sato, K., Takui, T. & Okada, K. (2007). Polyhedron, 26, 2021-2026.]). For coordination properties of nitronyl nitroxides, see: Masuda et al. (2009[Masuda, Y., Kurats, M., Suzuki, S., Kozaki, M., Shiomi, D., Sato, K., Takui, T., Hosokoshi, Y., Miyazaki, Y., Inada, A. & Okada, K. (2009). J. Am. Chem. Soc. 131, 4670-4673.]). For related structures, see: Wang et al. (2009[Wang, H.-B., Jing, L.-L., Gao, P. & Sun, X.-L. (2009). Acta Cryst. E65, o2090.]); Jing et al. (2009[Jing, L.-L., Wang, H.-B. & Sun, X.-L. (2009). Acta Cryst. E65, o2444.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For pseudorotation parameters, see: Rao et al. (1981[Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421-425.]).

[Scheme 1]

Experimental

Crystal data

  • C15H21N2O4

  • Mr = 293.34

  • Orthorhombic, P b c a

  • a = 8.869 (3) Å

  • b = 16.050 (5) Å

  • c = 20.925 (6) Å

  • V = 2978.7 (16) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.26 × 0.23 × 0.22 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.979

  • 20164 measured reflections

  • 2774 independent reflections

  • 1928 reflections with I > 2σ(I)

  • Rint = 0.054
Refinement

  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.163

  • S = 0.95

  • 2774 reflections

  • 195 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the benzene C4–C9 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O4—H4⋯O2i 0.82 2.01 2.828 (3) 173
C12—H12C⋯O1ii 0.96 2.54 3.418 (3) 152
C15—H15C⋯Cg2iii 0.96 2.80 3.570 (3) 138
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681104815X/is5006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104815X/is5006Isup2.hkl

checkCIF report


Comment top

Nitronyl nitroxides, firstly synthesized more than 30 years ago, can be used for coordination with many metal cations, such as Mn2+, Cu2+ and Ni2+ leading to form some molecule-based magnetic materials (Masuda et al., 2009). They can also react with free radicals such as OH, H2O2 and O2 (Blasig et al., 2002) to protect cells from the attack of free radicals. So they have a lot of biological properties as anticancer, antiradiation and antioxidation (Qin et al., 2009; Tanaka et al., 2007; Soule et al., 2007).

The molecular structure of the title compound is shown in Fig. 1. The least-squares plane of the nitronyl nitroxide ring and the benzene ring are twisted with respect to each other making a dihedral angle of 33.50 (12)°. The puckering parameters of the nitronyl nitroxide ring are Q(2) = 0.177 (2) Å and φ = 237.1 (7)° (Cremer & Pople, 1975). The pseudorotation parameters (Rao et al., 1981) for the nitronyl nitroxide ring are P = 39.7 (4)° and τ(M) = 18.2 (1) ° for the C1—N1 reference bond with the closest puckering descriptor being twisted on C1—C2. The crystal structure is stabilized by O—H···O, C—H···O and C—H···π hydrogen bonds (Table 1).

Related literature top

For the preparation of the title compound, see: Ullman et al. (1974). For biological properties of nitronyl nitroxides, see: Soule et al. (2007); Blasig et al. (2002); Qin et al. (2009); Tanaka et al. (2007). For coordination properties of nitronyl nitroxides, see: Masuda et al. (2009). For related structures, see: Wang et al. (2009); Jing et al. (2009). For puckering parameters, see: Cremer & Pople (1975). For pseudorotation parameters, see: Rao et al. (1981).

Experimental top

2,3-Dimethyl-2,3-bis(hydroxylamino) butane (1.48 g, 10.0 mmol) and 4-(4-hydroxyethoxy)benzaldehyde (1.66 g, 10 mmol) were dissolved in methanol (30.0 ml). The reaction was filtered after stirring for 24 h at room temperature. The resulting white powder was washed by cool methanol and suspended in the solution of dichloromethane (30.0 ml). Then the reaction mixture was added to an aqueous solution of NaIO4(30 ml) and stirred for 15 min in an ice bath to give a dark blue solution. The aqueous phase was extracted with CH2Cl2 and the organic layer was combined and dried over Na2SO4. Then the solvent was removed to give a dark blue residue which was purified by flash column chromatography with the elution of n-hexane/ ethyl acetate (1:2) to yield 1.61 g (55%) of the title compound as a dark blue powder. Single crystals of the title compound suitable for X-ray diffraction was recrystallized from hexane/dichloromethane (1:1).

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.96 Å (methyl), 0.97 Å (methylene) or 0.93 Å (aryl), and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Structure description top

Nitronyl nitroxides, firstly synthesized more than 30 years ago, can be used for coordination with many metal cations, such as Mn2+, Cu2+ and Ni2+ leading to form some molecule-based magnetic materials (Masuda et al., 2009). They can also react with free radicals such as OH, H2O2 and O2 (Blasig et al., 2002) to protect cells from the attack of free radicals. So they have a lot of biological properties as anticancer, antiradiation and antioxidation (Qin et al., 2009; Tanaka et al., 2007; Soule et al., 2007).

The molecular structure of the title compound is shown in Fig. 1. The least-squares plane of the nitronyl nitroxide ring and the benzene ring are twisted with respect to each other making a dihedral angle of 33.50 (12)°. The puckering parameters of the nitronyl nitroxide ring are Q(2) = 0.177 (2) Å and φ = 237.1 (7)° (Cremer & Pople, 1975). The pseudorotation parameters (Rao et al., 1981) for the nitronyl nitroxide ring are P = 39.7 (4)° and τ(M) = 18.2 (1) ° for the C1—N1 reference bond with the closest puckering descriptor being twisted on C1—C2. The crystal structure is stabilized by O—H···O, C—H···O and C—H···π hydrogen bonds (Table 1).

For the preparation of the title compound, see: Ullman et al. (1974). For biological properties of nitronyl nitroxides, see: Soule et al. (2007); Blasig et al. (2002); Qin et al. (2009); Tanaka et al. (2007). For coordination properties of nitronyl nitroxides, see: Masuda et al. (2009). For related structures, see: Wang et al. (2009); Jing et al. (2009). For puckering parameters, see: Cremer & Pople (1975). For pseudorotation parameters, see: Rao et al. (1981).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007; 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: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
2-[4-(2-Hydroxyethoxy)phenyl]-4,4,5,5-tetramethyl-2-imidazoline-1-oxyl 3-oxide top
Crystal data top
C15H21N2O4F(000) = 1256
Mr = 293.34Dx = 1.308 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3005 reflections
a = 8.869 (3) Åθ = 2.5–21.6°
b = 16.050 (5) ŵ = 0.10 mm−1
c = 20.925 (6) ÅT = 296 K
V = 2978.7 (16) Å3Block, blue
Z = 80.26 × 0.23 × 0.22 mm
Data collection top
Bruker APEXII CCD
diffractometer		2774 independent reflections
Radiation source: fine-focus sealed tube1928 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −10→10
Tmin = 0.976, Tmax = 0.979k = −17→19
20164 measured reflectionsl = −25→25
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.1P)2 + 0.8575P]
where P = (Fo2 + 2Fc2)/3
2774 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C15H21N2O4V = 2978.7 (16) Å3
Mr = 293.34Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 8.869 (3) ŵ = 0.10 mm−1
b = 16.050 (5) ÅT = 296 K
c = 20.925 (6) Å0.26 × 0.23 × 0.22 mm
Data collection top
Bruker APEXII CCD
diffractometer		2774 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		1928 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.979Rint = 0.054
20164 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.163H-atom parameters constrained
S = 0.95Δρmax = 0.22 e Å−3
2774 reflectionsΔρmin = −0.25 e Å−3
195 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
C10.8584 (2)1.12763 (14)0.33524 (10)0.0381 (5)
C20.8507 (3)1.05283 (14)0.38244 (10)0.0401 (5)
C30.8131 (2)1.00297 (13)0.27718 (9)0.0338 (5)
C40.7901 (2)0.94682 (13)0.22347 (9)0.0333 (5)
C50.6890 (3)0.88085 (13)0.22601 (10)0.0405 (5)
H50.63430.87190.26330.049*
C60.6678 (3)0.82848 (13)0.17472 (10)0.0405 (5)
H60.59860.78510.17730.049*
C70.7503 (3)0.84085 (13)0.11912 (9)0.0351 (5)
C80.8535 (3)0.90560 (15)0.11621 (10)0.0417 (6)
H80.90980.91360.07920.050*
C90.8733 (3)0.95792 (14)0.16734 (10)0.0399 (6)
H90.94271.00120.16470.048*
C100.6427 (3)0.72306 (15)0.06578 (10)0.0463 (6)
H10A0.54080.73950.07700.056*
H10B0.67780.68290.09710.056*
C110.6449 (3)0.68517 (19)0.00040 (12)0.0586 (7)
H11A0.57800.6374−0.00070.070*
H11B0.60870.7255−0.03050.070*
C120.7205 (3)1.18423 (16)0.33598 (13)0.0550 (7)
H12A0.72751.22360.30160.083*
H12B0.71611.21350.37590.083*
H12C0.63111.15120.33090.083*
C131.0013 (3)1.17980 (17)0.33876 (13)0.0569 (7)
H13A1.08711.14520.33000.085*
H13B1.01061.20340.38070.085*
H13C0.99621.22380.30770.085*
C140.7400 (4)1.06293 (18)0.43721 (12)0.0653 (8)
H14A0.64131.07410.42040.098*
H14B0.77111.10850.46380.098*
H14C0.73751.01260.46200.098*
C151.0041 (3)1.02474 (19)0.40759 (13)0.0638 (8)
H15A0.99290.97330.43050.096*
H15B1.04401.06650.43570.096*
H15C1.07201.01670.37240.096*
N10.8557 (2)1.08321 (11)0.27221 (8)0.0368 (4)
N20.7976 (2)0.98429 (11)0.33930 (8)0.0374 (5)
O10.8756 (2)1.12342 (10)0.21999 (7)0.0558 (5)
O20.7595 (2)0.91285 (10)0.36180 (7)0.0581 (5)
O30.73915 (18)0.79412 (10)0.06528 (7)0.0464 (4)
O40.7906 (3)0.66024 (15)−0.01595 (10)0.0783 (7)
H40.78900.6369−0.05080.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0401 (12)0.0392 (13)0.0350 (11)−0.0033 (10)0.0006 (9)−0.0095 (9)
C20.0493 (13)0.0421 (13)0.0288 (10)−0.0015 (10)−0.0004 (9)−0.0067 (9)
C30.0397 (11)0.0330 (12)0.0289 (10)0.0003 (10)0.0010 (8)0.0005 (8)
C40.0399 (12)0.0319 (11)0.0280 (10)0.0023 (9)−0.0011 (8)0.0003 (8)
C50.0521 (13)0.0402 (13)0.0293 (10)−0.0037 (11)0.0089 (9)−0.0004 (9)
C60.0537 (14)0.0347 (12)0.0331 (11)−0.0076 (10)0.0056 (10)−0.0016 (9)
C70.0421 (12)0.0342 (11)0.0289 (10)0.0037 (9)−0.0009 (9)−0.0045 (8)
C80.0444 (12)0.0491 (14)0.0315 (11)−0.0040 (11)0.0113 (9)−0.0042 (9)
C90.0422 (13)0.0423 (13)0.0352 (11)−0.0078 (10)0.0065 (9)−0.0050 (9)
C100.0536 (14)0.0489 (14)0.0363 (11)−0.0112 (11)−0.0006 (10)−0.0037 (10)
C110.0661 (18)0.0676 (18)0.0420 (14)−0.0164 (14)−0.0063 (12)−0.0132 (12)
C120.0545 (16)0.0485 (15)0.0621 (16)0.0082 (12)−0.0003 (12)−0.0064 (12)
C130.0537 (16)0.0619 (17)0.0550 (15)−0.0171 (13)−0.0008 (12)−0.0081 (13)
C140.092 (2)0.0601 (17)0.0438 (14)−0.0058 (15)0.0248 (14)−0.0106 (12)
C150.0679 (18)0.0708 (19)0.0527 (15)0.0060 (15)−0.0233 (14)0.0018 (13)
N10.0449 (11)0.0363 (10)0.0293 (9)−0.0035 (8)0.0014 (7)−0.0010 (7)
N20.0505 (11)0.0355 (10)0.0261 (8)−0.0023 (8)0.0013 (7)0.0005 (7)
O10.0892 (14)0.0420 (10)0.0363 (9)−0.0110 (9)0.0059 (8)0.0083 (7)
O20.0993 (14)0.0428 (10)0.0322 (8)−0.0155 (10)0.0016 (8)0.0072 (7)
O30.0640 (11)0.0435 (9)0.0317 (8)−0.0112 (8)0.0074 (7)−0.0106 (6)
O40.0952 (17)0.0864 (16)0.0532 (12)0.0100 (13)0.0002 (10)−0.0280 (10)
Geometric parameters (Å, º) top
C1—N11.499 (3)C10—C111.497 (3)
C1—C131.520 (3)C10—H10A0.9700
C1—C121.524 (3)C10—H10B0.9700
C1—C21.556 (3)C11—O41.395 (3)
C2—N21.499 (3)C11—H11A0.9700
C2—C141.518 (3)C11—H11B0.9700
C2—C151.527 (4)C12—H12A0.9600
C3—N21.341 (3)C12—H12B0.9600
C3—N11.346 (3)C12—H12C0.9600
C3—C41.455 (3)C13—H13A0.9600
C4—C51.389 (3)C13—H13B0.9600
C4—C91.398 (3)C13—H13C0.9600
C5—C61.376 (3)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—C71.389 (3)C14—H14C0.9600
C6—H60.9300C15—H15A0.9600
C7—O31.357 (2)C15—H15B0.9600
C7—C81.386 (3)C15—H15C0.9600
C8—C91.371 (3)N1—O11.281 (2)
C8—H80.9300N2—O21.285 (2)
C9—H90.9300O4—H40.8200
C10—O31.426 (3)
N1—C1—C13108.57 (17)O4—C11—C10110.7 (2)
N1—C1—C12106.21 (18)O4—C11—H11A109.5
C13—C1—C12109.9 (2)C10—C11—H11A109.5
N1—C1—C2101.00 (16)O4—C11—H11B109.5
C13—C1—C2115.53 (19)C10—C11—H11B109.5
C12—C1—C2114.71 (19)H11A—C11—H11B108.1
N2—C2—C14109.3 (2)C1—C12—H12A109.5
N2—C2—C15105.71 (19)C1—C12—H12B109.5
C14—C2—C15110.4 (2)H12A—C12—H12B109.5
N2—C2—C1101.41 (16)C1—C12—H12C109.5
C14—C2—C1115.2 (2)H12A—C12—H12C109.5
C15—C2—C1114.0 (2)H12B—C12—H12C109.5
N2—C3—N1108.50 (17)C1—C13—H13A109.5
N2—C3—C4126.58 (19)C1—C13—H13B109.5
N1—C3—C4124.91 (18)H13A—C13—H13B109.5
C5—C4—C9118.04 (18)C1—C13—H13C109.5
C5—C4—C3122.21 (18)H13A—C13—H13C109.5
C9—C4—C3119.75 (19)H13B—C13—H13C109.5
C6—C5—C4121.61 (19)C2—C14—H14A109.5
C6—C5—H5119.2C2—C14—H14B109.5
C4—C5—H5119.2H14A—C14—H14B109.5
C5—C6—C7119.6 (2)C2—C14—H14C109.5
C5—C6—H6120.2H14A—C14—H14C109.5
C7—C6—H6120.2H14B—C14—H14C109.5
O3—C7—C8115.21 (18)C2—C15—H15A109.5
O3—C7—C6125.3 (2)C2—C15—H15B109.5
C8—C7—C6119.47 (18)H15A—C15—H15B109.5
C9—C8—C7120.63 (19)C2—C15—H15C109.5
C9—C8—H8119.7H15A—C15—H15C109.5
C7—C8—H8119.7H15B—C15—H15C109.5
C8—C9—C4120.6 (2)O1—N1—C3125.90 (17)
C8—C9—H9119.7O1—N1—C1120.55 (17)
C4—C9—H9119.7C3—N1—C1113.06 (16)
O3—C10—C11108.08 (19)O2—N2—C3125.57 (17)
O3—C10—H10A110.1O2—N2—C2121.12 (16)
C11—C10—H10A110.1C3—N2—C2112.80 (17)
O3—C10—H10B110.1C7—O3—C10118.67 (16)
C11—C10—H10B110.1C11—O4—H4109.5
H10A—C10—H10B108.4
N1—C1—C2—N2−16.7 (2)N2—C3—N1—O1−177.2 (2)
C13—C1—C2—N2−133.60 (19)C4—C3—N1—O13.5 (3)
C12—C1—C2—N297.0 (2)N2—C3—N1—C1−5.2 (2)
N1—C1—C2—C14−134.5 (2)C4—C3—N1—C1175.45 (19)
C13—C1—C2—C14108.6 (2)C13—C1—N1—O1−51.1 (3)
C12—C1—C2—C14−20.8 (3)C12—C1—N1—O167.0 (2)
N1—C1—C2—C1596.4 (2)C2—C1—N1—O1−172.97 (19)
C13—C1—C2—C15−20.5 (3)C13—C1—N1—C3136.5 (2)
C12—C1—C2—C15−149.9 (2)C12—C1—N1—C3−105.4 (2)
N2—C3—C4—C529.5 (3)C2—C1—N1—C314.6 (2)
N1—C3—C4—C5−151.3 (2)N1—C3—N2—O2−179.3 (2)
N2—C3—C4—C9−149.5 (2)C4—C3—N2—O20.0 (4)
N1—C3—C4—C929.7 (3)N1—C3—N2—C2−7.4 (2)
C9—C4—C5—C6−1.3 (3)C4—C3—N2—C2171.86 (19)
C3—C4—C5—C6179.6 (2)C14—C2—N2—O2−49.8 (3)
C4—C5—C6—C70.7 (4)C15—C2—N2—O269.0 (3)
C5—C6—C7—O3−179.5 (2)C1—C2—N2—O2−171.79 (19)
C5—C6—C7—C80.3 (3)C14—C2—N2—C3138.0 (2)
O3—C7—C8—C9179.1 (2)C15—C2—N2—C3−103.3 (2)
C6—C7—C8—C9−0.8 (3)C1—C2—N2—C315.9 (2)
C7—C8—C9—C40.2 (3)C8—C7—O3—C10176.0 (2)
C5—C4—C9—C80.8 (3)C6—C7—O3—C10−4.1 (3)
C3—C4—C9—C8179.9 (2)C11—C10—O3—C7177.4 (2)
O3—C10—C11—O460.5 (3)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the benzene C4–C9 ring.
D—H···AD—HH···AD···AD—H···A
O4—H4···O2i0.822.012.828 (3)173
C12—H12C···O1ii0.962.543.418 (3)152
C15—H15C···Cg2iii0.962.803.570 (3)138
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1/2, y, −z+1/2; (iii) x+1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formulaC15H21N2O4
Mr293.34
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)8.869 (3), 16.050 (5), 20.925 (6)
V (Å3)2978.7 (16)
Z8
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.26 × 0.23 × 0.22
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.976, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections		20164, 2774, 1928
Rint0.054
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.163, 0.95
No. of reflections2774
No. of parameters195
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SAINT (Bruker, 2007, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the benzene C4–C9 ring.
D—H···AD—HH···AD···AD—H···A
O4—H4···O2i0.822.012.828 (3)173
C12—H12C···O1ii0.962.543.418 (3)152
C15—H15C···Cg2iii0.962.803.570 (3)138
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1/2, y, −z+1/2; (iii) x+1/2, y, −z+1/2.
 

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 30772773, 30472186) for financial support.

References

First citationBlasig, I. E., Mertsch, K. & Haseloff, R. F. (2002). Neuropharmacology, 43, 1006–1014.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationJing, L.-L., Wang, H.-B. & Sun, X.-L. (2009). Acta Cryst. E65, o2444.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationMasuda, Y., Kurats, M., Suzuki, S., Kozaki, M., Shiomi, D., Sato, K., Takui, T., Hosokoshi, Y., Miyazaki, Y., Inada, A. & Okada, K. (2009). J. Am. Chem. Soc. 131, 4670–4673.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationQin, X. Y., Ding, G. R. & Sun, X. L. (2009). J. Chem. Res. pp. 511–514.  Web of Science CrossRef CAS Google Scholar
 First citationRao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421–425.  CrossRef CAS 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 citationSoule, B. P., Hyodo, F., Matsumoto, K., Simone, N. L., Cook, J. A., Krishna, M. C. & Mitchell, J. B. (2007). Free Radic. Biol. Med. 42, 1632–1650.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTanaka, K., Furuichi, K., Kozaki, M., Suzuki, S., Shiomi, D., Sato, K., Takui, T. & Okada, K. (2007). Polyhedron, 26, 2021–2026.  Web of Science CSD CrossRef CAS Google Scholar
 First citationUllman, E. F., Osiecki, J. H., Boocock, D. G. B. & Darcy, R. (1974). J. Am. Chem. Soc. 96, 7049–7053.  Google Scholar
 First citationWang, H.-B., Jing, L.-L., Gao, P. & Sun, X.-L. (2009). Acta Cryst. E65, o2090.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3348
https://doi.org/10.1107/S160053681104815X
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