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

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ISSN: 2056-9890

9,9-Di­methyl-12-(4-nitro­phen­yl)-9,10-di­hydro-12H-benzo[a]xanthen-11(8H)-one

aDepartment of Chemistry, Tangshan Normal College, Tangshan 063000, People's Republic of China
*Correspondence e-mail: deling1@126.com

(Received 30 October 2009; accepted 16 November 2009; online 21 November 2009)

In the mol­ecular structure of the title compound, C25H21NO4, the pyran ring adopts a flattened boat conformation, while the cyclo­hexenone ring is in an envelope conformation. The 4-nitro­phenyl ring is almost perpendicular to the pyran ring [dihedral angle = 89.39 (1)°]. In the crystal, mol­ecules are connected by inter­molecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of xanthenes and benzoxanthenes, see: Lambert et al. (1997[Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9706178 A1.]); Poupelin et al. (1978[Poupelin, J. P., Saint-Ruf, G., Foussard-Blanpin, O., Narcisse, G., Uchida-Ernouf, G. & Lacroix, R. (1978). Eur. J. Med. Chem. 13, 67-71.]); Ion et al. (1998[Ion, R.-M., Planner, A., Wiktorowicz, K. & Frackowiak, D. (1998). Acta Biochim. Pol. 45, 833-845.]); Saint-Ruf et al. (1975[Saint-Ruf, G., Hieu, H. T. & Poupelin, J. P. (1975). Naturwissenschaften, 62, 584-585.]).

[Scheme 1]

Experimental

Crystal data
  • C25H21NO4

  • Mr = 399.43

  • Monoclinic, C 2/c

  • a = 24.178 (5) Å

  • b = 11.078 (2) Å

  • c = 17.481 (4) Å

  • β = 119.78 (3)°

  • V = 4063.9 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.10 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.983, Tmax = 0.999

  • 14653 measured reflections

  • 4007 independent reflections

  • 3106 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.153

  • S = 1.03

  • 4007 reflections

  • 274 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O4i 0.95 2.42 3.323 (3) 159
C6—H6⋯O2ii 0.95 2.45 3.384 (3) 168
C18—H18B⋯O2iii 0.98 2.43 3.355 (2) 158
Symmetry codes: (i) [-x, y-1, -z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); 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: SHELXTL.

Supporting information


Comment top

Xanthenes and benzoxanthenes are biologically important drug intermediates. They are cited as active oxygen heterocycles possessing anti-inflammatory (Poupelin et al., 1978) and antiviral (Lambert et al., 1997) activity. These compounds are also utilized as antagonists for paralyzing action of zoxazolamine (Saint-Ruf et al., 1975) and in photodynamic therapy (Ion et al., 1998). We report herein the crystal structure of the title compound, which belongs to this class of compounds.

The pyran ring of the title molecule (Fig. 1) adopts a flattened boat conformation. The cyclohexenone ring is in an envelope conformation with atom C15 at the flap. The 4-nitrophenyl ring and the planar part of the pyran ring (C1/C10/C12/C17) are nearly perpendicular to each other, with a dihedral angle of 89.39 (1)°. In the crystal, the molecules are connected by C—H···O hydrogen bonds (Fig. 2).

Related literature top

For the biological activity of xanthenes and benzoxanthenes, see: Lambert et al. (1997); Poupelin et al. (1978); Ion et al. (1998); Saint-Ruf et al. (1975).

Experimental top

To a mixture of 2-naphthol (1.0 mmol), benzaldehyde (1.0 mmol), and 5,5-dimethylcyclohexane-1,3-dione (1.1 mmol) was added strontium trifluoromethanesulfonate (0.1 mmol) in 1,2-dichloroethane (2 ml). The mixture was stirred at 353 K for 5 h. The progress of the reaction was monitored by TLC. After completion of the reaction, water was added and the product was extracted with ethyl acetate (3×10 ml). The organic layer was dried (MgSO4) and evaporated, and the crude product was purified by flash chromatography on silica gel. Pure product crystallized slowly at room temperature in ethanol. A single-crystal was obtained by slow evaporation of a solution in ethanol.

Refinement top

H atoms were included in the refinement in the riding and rotation model approximation, with C—H = 0.95–1.00 Å and Uiso (H) = 1.2 Ueq(Carrier atom). For the methyl H atoms, Uiso(H) = 1.5Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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. A view of the molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The packing, showing hydrogen-bond interactions as dashed lines; H atoms are shown as small spheres of arbitrary radii.
9,9-Dimethyl-12-(4-nitrophenyl)-9,10-dihydro-12H- benzo[a]xanthen-11(8H)-one top
Crystal data top
C25H21NO4F(000) = 1680
Mr = 399.43Dx = 1.306 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4847 reflections
a = 24.178 (5) Åθ = 2.1–27.9°
b = 11.078 (2) ŵ = 0.09 mm1
c = 17.481 (4) ÅT = 113 K
β = 119.78 (3)°Prism, yellow
V = 4063.9 (19) Å30.20 × 0.18 × 0.10 mm
Z = 8
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
4007 independent reflections
Radiation source: rotating anode3106 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.044
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 2.1°
ω and ϕ scansh = 2926
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1312
Tmin = 0.983, Tmax = 0.999l = 1821
14653 measured reflections
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) = 0.153 w = 1/[σ2(Fo2) + (0.0882P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4007 reflectionsΔρmax = 0.29 e Å3
274 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0043 (6)
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H21NO4V = 4063.9 (19) Å3
Mr = 399.43Z = 8
Monoclinic, C2/cMo Kα radiation
a = 24.178 (5) ŵ = 0.09 mm1
b = 11.078 (2) ÅT = 113 K
c = 17.481 (4) Å0.20 × 0.18 × 0.10 mm
β = 119.78 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
4007 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
3106 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.999Rint = 0.044
14653 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å3
4007 reflectionsΔρmin = 0.26 e Å3
274 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.07668 (6)0.09846 (11)0.23338 (8)0.0274 (3)
O20.23273 (6)0.17081 (12)0.24963 (8)0.0360 (4)
O30.06051 (8)0.52066 (14)0.42025 (11)0.0504 (5)
O40.08357 (10)0.64016 (14)0.34280 (11)0.0625 (5)
N10.07521 (9)0.53889 (15)0.36366 (11)0.0385 (5)
C10.02775 (9)0.03873 (17)0.16146 (11)0.0247 (4)
C20.03123 (9)0.09880 (17)0.12366 (12)0.0295 (5)
H20.03510.17380.14690.035*
C30.08261 (9)0.04833 (18)0.05346 (12)0.0321 (5)
H30.12270.08800.02830.038*
C40.07735 (9)0.06226 (18)0.01731 (12)0.0292 (5)
C50.13056 (10)0.1170 (2)0.05572 (13)0.0365 (5)
H50.17100.07870.08050.044*
C60.12508 (10)0.2230 (2)0.09105 (13)0.0397 (6)
H60.16150.25910.13880.048*
C70.06498 (10)0.2782 (2)0.05608 (12)0.0370 (5)
H70.06070.35050.08190.044*
C80.01239 (9)0.22896 (17)0.01486 (11)0.0295 (5)
H80.02770.26830.03780.035*
C90.01689 (8)0.12084 (17)0.05423 (11)0.0243 (4)
C100.03670 (8)0.06891 (16)0.13055 (11)0.0230 (4)
C110.10058 (8)0.13313 (16)0.17849 (11)0.0233 (4)
H110.11190.16280.13400.028*
C120.15111 (8)0.04569 (16)0.23939 (11)0.0237 (4)
C130.21800 (9)0.07594 (17)0.27101 (11)0.0263 (4)
C140.26749 (9)0.01679 (17)0.32757 (12)0.0291 (5)
H14A0.30890.02440.36350.035*
H14B0.27270.07520.28870.035*
C150.25060 (9)0.08591 (16)0.38902 (11)0.0278 (4)
C160.18478 (9)0.14376 (17)0.33158 (12)0.0276 (4)
H16A0.18930.21400.30010.033*
H16B0.16860.17360.37010.033*
C170.13742 (9)0.05788 (16)0.26568 (11)0.0241 (4)
C180.30005 (10)0.18485 (18)0.43696 (13)0.0361 (5)
H18A0.34250.14840.47020.054*
H18B0.29950.24210.39380.054*
H18C0.28990.22750.47760.054*
C190.24992 (10)0.00103 (19)0.45700 (12)0.0350 (5)
H19A0.29130.04180.48920.052*
H19B0.24180.04450.49850.052*
H19C0.21630.06130.42660.052*
C200.09628 (8)0.24126 (16)0.22956 (11)0.0232 (4)
C210.10351 (9)0.35856 (17)0.20785 (12)0.0285 (4)
H210.11290.37160.16170.034*
C220.09739 (10)0.45691 (18)0.25190 (12)0.0323 (5)
H220.10230.53690.23660.039*
C230.08393 (9)0.43547 (16)0.31859 (12)0.0276 (4)
C240.07792 (9)0.32046 (17)0.34403 (12)0.0293 (5)
H240.06980.30810.39140.035*
C250.08398 (9)0.22379 (17)0.29877 (11)0.0270 (4)
H250.07970.14400.31510.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0245 (7)0.0279 (7)0.0284 (7)0.0022 (5)0.0120 (6)0.0018 (5)
O20.0243 (7)0.0399 (9)0.0376 (8)0.0038 (6)0.0108 (6)0.0098 (6)
O30.0587 (11)0.0439 (10)0.0597 (10)0.0063 (8)0.0378 (9)0.0174 (8)
O40.1033 (16)0.0236 (9)0.0641 (11)0.0058 (9)0.0444 (11)0.0003 (8)
N10.0419 (11)0.0297 (10)0.0373 (10)0.0006 (8)0.0146 (8)0.0073 (8)
C10.0236 (10)0.0268 (10)0.0230 (9)0.0009 (7)0.0110 (7)0.0040 (7)
C20.0292 (11)0.0291 (10)0.0342 (10)0.0044 (8)0.0189 (8)0.0061 (8)
C30.0240 (11)0.0381 (12)0.0352 (11)0.0068 (8)0.0155 (8)0.0149 (9)
C40.0229 (10)0.0370 (11)0.0268 (10)0.0015 (8)0.0116 (8)0.0099 (8)
C50.0223 (10)0.0499 (14)0.0295 (10)0.0035 (9)0.0070 (8)0.0131 (9)
C60.0316 (12)0.0508 (14)0.0271 (10)0.0158 (10)0.0073 (8)0.0033 (10)
C70.0407 (13)0.0418 (13)0.0253 (10)0.0114 (10)0.0140 (9)0.0018 (9)
C80.0288 (11)0.0347 (11)0.0238 (9)0.0054 (8)0.0123 (8)0.0012 (8)
C90.0198 (10)0.0301 (10)0.0230 (9)0.0025 (8)0.0106 (7)0.0062 (7)
C100.0214 (10)0.0268 (10)0.0224 (9)0.0006 (7)0.0120 (7)0.0037 (7)
C110.0208 (9)0.0258 (10)0.0237 (9)0.0000 (7)0.0113 (7)0.0006 (7)
C120.0216 (10)0.0270 (10)0.0213 (9)0.0005 (7)0.0097 (7)0.0005 (7)
C130.0243 (10)0.0308 (11)0.0232 (9)0.0001 (8)0.0113 (8)0.0012 (8)
C140.0213 (10)0.0326 (11)0.0305 (10)0.0031 (8)0.0107 (8)0.0007 (8)
C150.0262 (11)0.0280 (10)0.0263 (10)0.0051 (8)0.0108 (8)0.0006 (8)
C160.0293 (11)0.0257 (10)0.0270 (9)0.0017 (8)0.0134 (8)0.0018 (8)
C170.0210 (10)0.0269 (10)0.0238 (9)0.0024 (7)0.0106 (7)0.0046 (7)
C180.0330 (12)0.0374 (12)0.0334 (10)0.0082 (9)0.0130 (8)0.0046 (9)
C190.0327 (11)0.0378 (12)0.0289 (10)0.0044 (9)0.0112 (8)0.0031 (9)
C200.0174 (9)0.0247 (10)0.0235 (9)0.0005 (7)0.0069 (7)0.0009 (7)
C210.0286 (10)0.0297 (10)0.0271 (9)0.0025 (8)0.0137 (8)0.0025 (8)
C220.0361 (12)0.0223 (10)0.0314 (10)0.0022 (8)0.0115 (9)0.0028 (8)
C230.0263 (10)0.0225 (10)0.0276 (10)0.0003 (8)0.0084 (8)0.0042 (8)
C240.0317 (11)0.0301 (11)0.0279 (10)0.0041 (8)0.0162 (8)0.0051 (8)
C250.0301 (10)0.0232 (10)0.0276 (10)0.0033 (8)0.0143 (8)0.0010 (8)
Geometric parameters (Å, º) top
O1—C171.362 (2)C12—C131.465 (3)
O1—C11.393 (2)C13—C141.513 (3)
O2—C131.226 (2)C14—C151.531 (3)
O3—N11.223 (2)C14—H14A0.9900
O4—N11.227 (2)C14—H14B0.9900
N1—C231.464 (2)C15—C181.529 (2)
C1—C101.370 (2)C15—C191.536 (3)
C1—C21.406 (3)C15—C161.538 (3)
C2—C31.359 (3)C16—C171.494 (3)
C2—H20.9500C16—H16A0.9900
C3—C41.413 (3)C16—H16B0.9900
C3—H30.9500C18—H18A0.9800
C4—C51.422 (3)C18—H18B0.9800
C4—C91.427 (3)C18—H18C0.9800
C5—C61.364 (3)C19—H19A0.9800
C5—H50.9500C19—H19B0.9800
C6—C71.406 (3)C19—H19C0.9800
C6—H60.9500C20—C211.389 (2)
C7—C81.373 (3)C20—C251.395 (3)
C7—H70.9500C21—C221.384 (3)
C8—C91.412 (3)C21—H210.9500
C8—H80.9500C22—C231.378 (3)
C9—C101.440 (2)C22—H220.9500
C10—C111.519 (2)C23—C241.381 (3)
C11—C121.507 (2)C24—C251.382 (2)
C11—C201.528 (2)C24—H240.9500
C11—H111.0000C25—H250.9500
C12—C171.337 (2)
C17—O1—C1118.36 (14)C13—C14—H14B108.9
O3—N1—O4123.25 (17)C15—C14—H14B108.9
O3—N1—C23118.92 (17)H14A—C14—H14B107.7
O4—N1—C23117.82 (18)C18—C15—C14109.56 (16)
C10—C1—O1122.67 (16)C18—C15—C19109.35 (15)
C10—C1—C2123.27 (17)C14—C15—C19109.78 (15)
O1—C1—C2114.06 (16)C18—C15—C16109.46 (15)
C3—C2—C1119.24 (19)C14—C15—C16107.49 (15)
C3—C2—H2120.4C19—C15—C16111.18 (16)
C1—C2—H2120.4C17—C16—C15112.73 (15)
C2—C3—C4121.03 (18)C17—C16—H16A109.0
C2—C3—H3119.5C15—C16—H16A109.0
C4—C3—H3119.5C17—C16—H16B109.0
C3—C4—C5121.93 (19)C15—C16—H16B109.0
C3—C4—C9119.44 (17)H16A—C16—H16B107.8
C5—C4—C9118.62 (19)C12—C17—O1122.74 (16)
C6—C5—C4121.7 (2)C12—C17—C16125.83 (17)
C6—C5—H5119.1O1—C17—C16111.42 (16)
C4—C5—H5119.1C15—C18—H18A109.5
C5—C6—C7119.32 (19)C15—C18—H18B109.5
C5—C6—H6120.3H18A—C18—H18B109.5
C7—C6—H6120.3C15—C18—H18C109.5
C8—C7—C6120.9 (2)H18A—C18—H18C109.5
C8—C7—H7119.6H18B—C18—H18C109.5
C6—C7—H7119.6C15—C19—H19A109.5
C7—C8—C9121.07 (19)C15—C19—H19B109.5
C7—C8—H8119.5H19A—C19—H19B109.5
C9—C8—H8119.5C15—C19—H19C109.5
C8—C9—C4118.34 (17)H19A—C19—H19C109.5
C8—C9—C10122.60 (17)H19B—C19—H19C109.5
C4—C9—C10119.05 (18)C21—C20—C25118.47 (16)
C1—C10—C9117.88 (17)C21—C20—C11121.29 (16)
C1—C10—C11120.43 (16)C25—C20—C11120.23 (16)
C9—C10—C11121.63 (16)C22—C21—C20121.44 (17)
C12—C11—C10109.51 (15)C22—C21—H21119.3
C12—C11—C20110.94 (14)C20—C21—H21119.3
C10—C11—C20110.11 (14)C23—C22—C21118.07 (17)
C12—C11—H11108.7C23—C22—H22121.0
C10—C11—H11108.7C21—C22—H22121.0
C20—C11—H11108.7C22—C23—C24122.59 (17)
C17—C12—C13118.81 (16)C22—C23—N1118.57 (17)
C17—C12—C11122.81 (17)C24—C23—N1118.85 (17)
C13—C12—C11118.38 (16)C23—C24—C25118.20 (17)
O2—C13—C12120.95 (17)C23—C24—H24120.9
O2—C13—C14121.74 (17)C25—C24—H24120.9
C12—C13—C14117.25 (16)C24—C25—C20121.19 (17)
C13—C14—C15113.47 (16)C24—C25—H25119.4
C13—C14—H14A108.9C20—C25—H25119.4
C15—C14—H14A108.9
C17—O1—C1—C1010.1 (2)C17—C12—C13—C143.6 (2)
C17—O1—C1—C2169.76 (15)C11—C12—C13—C14176.40 (15)
C10—C1—C2—C30.7 (3)O2—C13—C14—C15146.74 (17)
O1—C1—C2—C3179.44 (15)C12—C13—C14—C1535.8 (2)
C1—C2—C3—C41.0 (3)C13—C14—C15—C18174.83 (15)
C2—C3—C4—C5179.58 (17)C13—C14—C15—C1965.1 (2)
C2—C3—C4—C91.0 (3)C13—C14—C15—C1656.0 (2)
C3—C4—C5—C6179.19 (18)C18—C15—C16—C17165.35 (15)
C9—C4—C5—C60.2 (3)C14—C15—C16—C1746.4 (2)
C4—C5—C6—C71.8 (3)C19—C15—C16—C1773.74 (19)
C5—C6—C7—C82.2 (3)C13—C12—C17—O1173.81 (15)
C6—C7—C8—C90.7 (3)C11—C12—C17—O16.2 (3)
C7—C8—C9—C41.3 (3)C13—C12—C17—C165.4 (3)
C7—C8—C9—C10177.74 (17)C11—C12—C17—C16174.52 (16)
C3—C4—C9—C8177.69 (16)C1—O1—C17—C129.3 (2)
C5—C4—C9—C81.7 (3)C1—O1—C17—C16170.01 (14)
C3—C4—C9—C103.3 (3)C15—C16—C17—C1217.8 (3)
C5—C4—C9—C10177.33 (16)C15—C16—C17—O1162.89 (14)
O1—C1—C10—C9178.31 (14)C12—C11—C20—C21123.51 (18)
C2—C1—C10—C91.6 (3)C10—C11—C20—C21115.09 (19)
O1—C1—C10—C114.4 (3)C12—C11—C20—C2557.4 (2)
C2—C1—C10—C11175.71 (16)C10—C11—C20—C2564.0 (2)
C8—C9—C10—C1177.50 (16)C25—C20—C21—C221.4 (3)
C4—C9—C10—C13.5 (3)C11—C20—C21—C22177.65 (17)
C8—C9—C10—C115.3 (3)C20—C21—C22—C230.1 (3)
C4—C9—C10—C11173.76 (15)C21—C22—C23—C241.5 (3)
C1—C10—C11—C1217.4 (2)C21—C22—C23—N1177.96 (17)
C9—C10—C11—C12165.45 (15)O3—N1—C23—C22176.83 (18)
C1—C10—C11—C20104.88 (19)O4—N1—C23—C223.7 (3)
C9—C10—C11—C2072.3 (2)O3—N1—C23—C242.7 (3)
C10—C11—C12—C1718.7 (2)O4—N1—C23—C24176.80 (19)
C20—C11—C12—C17103.10 (19)C22—C23—C24—C251.8 (3)
C10—C11—C12—C13161.39 (15)N1—C23—C24—C25177.68 (17)
C20—C11—C12—C1376.85 (19)C23—C24—C25—C200.4 (3)
C17—C12—C13—O2178.88 (17)C21—C20—C25—C241.1 (3)
C11—C12—C13—O21.1 (3)C11—C20—C25—C24177.95 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O4i0.952.423.323 (3)159
C6—H6···O2ii0.952.453.384 (3)168
C18—H18B···O2iii0.982.433.355 (2)158
Symmetry codes: (i) x, y1, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC25H21NO4
Mr399.43
Crystal system, space groupMonoclinic, C2/c
Temperature (K)113
a, b, c (Å)24.178 (5), 11.078 (2), 17.481 (4)
β (°) 119.78 (3)
V3)4063.9 (19)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.18 × 0.10
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.983, 0.999
No. of measured, independent and
observed [I > 2σ(I)] reflections
14653, 4007, 3106
Rint0.044
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.153, 1.03
No. of reflections4007
No. of parameters274
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.26

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O4i0.952.423.323 (3)158.5
C6—H6···O2ii0.952.453.384 (3)168.3
C18—H18B···O2iii0.982.433.355 (2)158.0
Symmetry codes: (i) x, y1, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+1/2.
 

Acknowledgements

The authors thank the Tangshan Municipal Science and Technology Commission (No. 07160213B) and Tangshan Normal College (No. 07 A02) for financial support.

References

First citationIon, R.-M., Planner, A., Wiktorowicz, K. & Frackowiak, D. (1998). Acta Biochim. Pol. 45, 833–845.  Web of Science CAS PubMed Google Scholar
First citationLambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9706178 A1.  Google Scholar
First citationPoupelin, J. P., Saint-Ruf, G., Foussard-Blanpin, O., Narcisse, G., Uchida-Ernouf, G. & Lacroix, R. (1978). Eur. J. Med. Chem. 13, 67–71.  CAS Google Scholar
First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSaint-Ruf, G., Hieu, H. T. & Poupelin, J. P. (1975). Naturwissenschaften, 62, 584–585.  CrossRef PubMed CAS 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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