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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

15-Meth­­oxy-14,15-di­hydro­andranginine

aSchool of Pharmacy, Anhui University of Traditional Chinese Medicine, Hefei 230038, People's Republic of China, and bState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China
*Correspondence e-mail: great7701@126.com, hhp760222@126.com

(Received 11 January 2013; accepted 28 April 2013; online 4 May 2013)

The title polycyclic alkaloid, C22H26N2O3, an indole derivative obtained from Melodinus yunnanensis, comprises three chiral C atoms and crystallizes as a racemate. Its seven-membered heterocyclic ring has a twisted conformation, with the N atom within the plane of the indole moiety and with two adjacent C atoms deviating in opposite directions from its plane by 0.756 (3) (methyl­ene C) and −0.802 (3) Å (methine C). In the crystal, pairs of N—H⋯O hydrogen bonds connect the mol­ecules into centrosymmetric dimers.

Related literature

Indole alkaloid derivatives obtained from Melodinus yunnanensis have been investigated due to their anti­malarial and anti­cancer properties, see: Kanfan et al. (1974[Kanfan, C., Massiot, G., Ahond, A., Das, B. C., Husson, H. P. & Potier, P. (1974). J. Chem. Soc. Chem Commun. pp. 164-165.]). For the structures of related compounds, see: Danieli et al. (1977a[Danieli, B., Lesma, G., Martinelli, M., Passarella, D. & Silvani, A. (1977a). J. Org. Chem. 19, 6519-6523.]) and for applications of similar compounds see: Danieli et al. (1977a[Danieli, B., Lesma, G., Martinelli, M., Passarella, D. & Silvani, A. (1977a). J. Org. Chem. 19, 6519-6523.],b[Danieli, B., Lesma, G., Luzzani, M., Passarella, D. & Silvani, A. (1977b). Tetrahedron, 34, 11291-11296.])

[Scheme 1]

Experimental

Crystal data
  • C22H26N2O3

  • Mr = 366.45

  • Triclinic, [P \overline 1]

  • a = 6.914 (3) Å

  • b = 11.232 (4) Å

  • c = 11.806 (4) Å

  • α = 91.079 (6)°

  • β = 100.737 (5)°

  • γ = 96.317 (6)°

  • V = 894.5 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 153 K

  • 0.43 × 0.23 × 0.13 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • 8672 measured reflections

  • 4028 independent reflections

  • 2868 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.089

  • S = 1.00

  • 4028 reflections

  • 250 parameters

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

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O3i 0.859 (17) 2.187 (16) 2.9759 (18) 152.6 (15)
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). 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: SHELXTL.

Supporting information


Comment top

The indole alkaloid derivatives of the title compound, (I), are obtained from Melodinus yunnanensis leaves and twigs by column chromatography. These indole alkaloid derivatives have been investigated due to their antimalarial and anticancer properties (Kanfan et al. 1974). Herewith we present the crystal structure of (I).

Related literature top

Indole alkaloid derivatives obtained from Melodinus yunnanensis have been investigated due to their antimalarial and anticancer properties, see: Kanfan et al. (1974). For the structures of related compounds, see: Danieli et al. (1977a) and for applications of similar compounds see: Danieli et al. (1977a,b)

Experimental top

Dried and powdered leaves and twigs of Melodinus yunnanensis (20 kg) were extracted three times with methanol at room temperature and the solvent evaporated in vacuo. The residue was dissolved in 0.3% aqueous hydrochloric acid, and the solution subsequently basified using ammonia water to pH 9–10. The basic solution was partitioned with EtOAc, producing an aqueous and EtOAc phase. The resulting EtOAc fraction (105 g) was collected and then subjected to column chromatography over silica gel and eluted with a chloroform-acetone gradient (1/0 to 3/1, v/v) to afford the title compound (500 mg). The product was purified by recrystalliaztion from methanol to give colorless crystals.

Refinement top

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.95-1.00 Å and Uiso(H) = 1.2 Ueq. Positions of hydrogen atoms of methyl groups were rotationally optimized. Atom H of amino group was refined isotropically without restrictions.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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 the title molecule(I) with atom labels and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. : packing diagram of (I). Hydrogen bonds shown as dashed lines.
15-Methoxy-14,15-dihydroandranginine top
Crystal data top
C22H26N2O3Z = 2
Mr = 366.45F(000) = 392
Triclinic, P1Dx = 1.361 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.914 (3) ÅCell parameters from 2653 reflections
b = 11.232 (4) Åθ = 3.0–27.5°
c = 11.806 (4) ŵ = 0.09 mm1
α = 91.079 (6)°T = 153 K
β = 100.737 (5)°Prism, colorless
γ = 96.317 (6)°0.43 × 0.23 × 0.13 mm
V = 894.5 (6) Å3
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
2868 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.030
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
Detector resolution: 28.5714 pixels mm-1h = 88
phi and ω scansk = 1414
8672 measured reflectionsl = 1415
4028 independent reflections
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0318P)2 + 0.160P]
where P = (Fo2 + 2Fc2)/3
4028 reflections(Δ/σ)max = 0.001
250 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C22H26N2O3γ = 96.317 (6)°
Mr = 366.45V = 894.5 (6) Å3
Triclinic, P1Z = 2
a = 6.914 (3) ÅMo Kα radiation
b = 11.232 (4) ŵ = 0.09 mm1
c = 11.806 (4) ÅT = 153 K
α = 91.079 (6)°0.43 × 0.23 × 0.13 mm
β = 100.737 (5)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
2868 reflections with I > 2σ(I)
8672 measured reflectionsRint = 0.030
4028 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.27 e Å3
4028 reflectionsΔρmin = 0.19 e Å3
250 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
O10.60683 (16)0.85999 (9)0.01190 (9)0.0277 (3)
O20.46541 (15)0.48350 (9)0.27560 (8)0.0239 (2)
O30.67895 (15)0.46849 (9)0.44057 (8)0.0244 (2)
N11.00622 (18)0.69322 (12)0.50300 (10)0.0205 (3)
N40.42553 (17)0.72717 (10)0.24809 (9)0.0185 (3)
C20.8300 (2)0.71262 (13)0.43152 (11)0.0175 (3)
C30.3346 (2)0.81220 (14)0.16762 (12)0.0229 (3)
H3A0.42080.88950.17580.028*
H3B0.20480.82690.18560.028*
C50.4122 (2)0.75869 (13)0.36721 (11)0.0194 (3)
H5A0.42150.68540.41230.023*
H5B0.27930.78400.36690.023*
C60.5671 (2)0.85711 (13)0.43018 (12)0.0215 (3)
H6A0.58760.92230.37690.026*
H6B0.51760.89110.49590.026*
C70.7607 (2)0.81020 (13)0.47397 (12)0.0189 (3)
C80.8993 (2)0.85448 (13)0.57542 (12)0.0201 (3)
C90.9085 (2)0.95044 (14)0.65452 (12)0.0246 (3)
H90.80691.00190.64570.030*
C101.0671 (2)0.96896 (14)0.74531 (13)0.0275 (4)
H101.07391.03360.79960.033*
C111.2176 (2)0.89460 (14)0.75890 (13)0.0280 (4)
H111.32610.91020.82170.034*
C121.2125 (2)0.79874 (14)0.68306 (12)0.0262 (4)
H121.31490.74780.69290.031*
C131.0515 (2)0.77946 (13)0.59135 (12)0.0202 (3)
C140.3065 (2)0.76125 (15)0.04513 (12)0.0259 (4)
H14A0.21990.68410.03710.031*
H14B0.24140.81730.00920.031*
C150.5046 (2)0.74198 (14)0.01609 (12)0.0235 (3)
H150.48460.69940.06110.028*
C160.7451 (2)0.63502 (12)0.32228 (11)0.0168 (3)
C170.9184 (2)0.59056 (13)0.27308 (12)0.0214 (3)
H17A1.01060.66080.26050.026*
H17B0.99200.54110.33080.026*
C180.8514 (2)0.51737 (14)0.16040 (12)0.0242 (3)
H18A0.96850.50190.12760.029*
H18B0.78120.43920.17500.029*
C190.7168 (2)0.58305 (13)0.07633 (12)0.0231 (3)
H190.69870.56060.00330.028*
C200.6212 (2)0.67091 (13)0.10661 (12)0.0200 (3)
C210.6292 (2)0.71353 (12)0.23085 (11)0.0177 (3)
H210.70390.79570.24040.021*
C220.7679 (3)0.86269 (17)0.04602 (15)0.0386 (4)
H22A0.83270.94500.04400.046*
H22B0.71990.83420.12640.046*
H22C0.86320.81070.00790.046*
C230.6256 (2)0.52135 (12)0.35387 (12)0.0174 (3)
C240.3361 (2)0.38405 (13)0.30607 (13)0.0250 (3)
H24A0.22270.36450.24270.030*
H24B0.28880.40610.37600.030*
H24C0.40920.31420.32020.030*
H1N1.078 (2)0.6370 (16)0.4959 (14)0.032 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0297 (6)0.0267 (6)0.0277 (6)0.0001 (5)0.0091 (5)0.0057 (5)
O20.0229 (6)0.0209 (6)0.0248 (6)0.0055 (4)0.0007 (5)0.0038 (4)
O30.0259 (6)0.0219 (6)0.0249 (6)0.0035 (4)0.0028 (5)0.0062 (4)
N10.0180 (7)0.0223 (7)0.0209 (7)0.0044 (5)0.0020 (5)0.0000 (5)
N40.0168 (6)0.0219 (7)0.0172 (6)0.0036 (5)0.0031 (5)0.0027 (5)
C20.0161 (7)0.0182 (7)0.0174 (7)0.0001 (6)0.0020 (6)0.0035 (6)
C30.0193 (8)0.0253 (8)0.0249 (8)0.0061 (6)0.0035 (6)0.0064 (6)
C50.0181 (7)0.0198 (8)0.0211 (7)0.0036 (6)0.0052 (6)0.0018 (6)
C60.0225 (8)0.0188 (8)0.0232 (8)0.0039 (6)0.0036 (6)0.0007 (6)
C70.0196 (7)0.0170 (7)0.0194 (7)0.0000 (6)0.0032 (6)0.0018 (6)
C80.0215 (8)0.0205 (8)0.0175 (7)0.0021 (6)0.0039 (6)0.0021 (6)
C90.0278 (9)0.0212 (8)0.0243 (8)0.0013 (6)0.0063 (7)0.0001 (6)
C100.0338 (9)0.0250 (8)0.0213 (8)0.0062 (7)0.0050 (7)0.0028 (6)
C110.0268 (9)0.0341 (9)0.0183 (8)0.0078 (7)0.0016 (7)0.0023 (7)
C120.0217 (8)0.0311 (9)0.0244 (8)0.0006 (7)0.0017 (7)0.0042 (7)
C130.0203 (8)0.0209 (8)0.0188 (7)0.0016 (6)0.0045 (6)0.0015 (6)
C140.0218 (8)0.0328 (9)0.0216 (8)0.0025 (7)0.0003 (6)0.0063 (7)
C150.0237 (8)0.0266 (8)0.0190 (7)0.0003 (6)0.0030 (6)0.0014 (6)
C160.0164 (7)0.0161 (7)0.0176 (7)0.0021 (6)0.0030 (6)0.0007 (5)
C170.0178 (7)0.0238 (8)0.0226 (8)0.0022 (6)0.0038 (6)0.0012 (6)
C180.0245 (8)0.0246 (8)0.0250 (8)0.0036 (6)0.0084 (7)0.0023 (6)
C190.0245 (8)0.0267 (8)0.0178 (7)0.0008 (6)0.0054 (6)0.0023 (6)
C200.0174 (7)0.0223 (8)0.0190 (7)0.0031 (6)0.0035 (6)0.0002 (6)
C210.0169 (7)0.0160 (7)0.0199 (7)0.0009 (6)0.0033 (6)0.0021 (6)
C220.0347 (10)0.0414 (11)0.0410 (10)0.0059 (8)0.0162 (8)0.0048 (8)
C230.0176 (7)0.0160 (7)0.0200 (7)0.0048 (6)0.0061 (6)0.0011 (6)
C240.0223 (8)0.0193 (8)0.0332 (9)0.0031 (6)0.0083 (7)0.0009 (6)
Geometric parameters (Å, º) top
O1—C221.4091 (19)C11—C121.381 (2)
O1—C151.4381 (18)C11—H110.9500
O2—C231.3274 (17)C12—C131.396 (2)
O2—C241.4461 (17)C12—H120.9500
O3—C231.2109 (16)C14—C151.509 (2)
N1—C131.3775 (19)C14—H14A0.9900
N1—C21.3881 (18)C14—H14B0.9900
N1—H1N0.859 (17)C15—C201.5105 (19)
N4—C51.4657 (18)C15—H151.0000
N4—C31.4675 (17)C16—C231.5337 (19)
N4—C211.4836 (18)C16—C171.549 (2)
C2—C71.366 (2)C16—C211.5665 (18)
C2—C161.5265 (19)C17—C181.518 (2)
C3—C141.515 (2)C17—H17A0.9900
C3—H3A0.9900C17—H17B0.9900
C3—H3B0.9900C18—C191.493 (2)
C5—C61.527 (2)C18—H18A0.9900
C5—H5A0.9900C18—H18B0.9900
C5—H5B0.9900C19—C201.325 (2)
C6—C71.498 (2)C19—H190.9500
C6—H6A0.9900C20—C211.523 (2)
C6—H6B0.9900C21—H211.0000
C7—C81.430 (2)C22—H22A0.9800
C8—C91.401 (2)C22—H22B0.9800
C8—C131.407 (2)C22—H22C0.9800
C9—C101.378 (2)C24—H24A0.9800
C9—H90.9500C24—H24B0.9800
C10—C111.393 (2)C24—H24C0.9800
C10—H100.9500
C22—O1—C15113.67 (12)C3—C14—H14B109.7
C23—O2—C24116.57 (11)H14A—C14—H14B108.2
C13—N1—C2109.27 (12)O1—C15—C14105.53 (12)
C13—N1—H1N123.4 (11)O1—C15—C20110.41 (12)
C2—N1—H1N127.3 (11)C14—C15—C20111.29 (12)
C5—N4—C3111.16 (11)O1—C15—H15109.8
C5—N4—C21114.27 (10)C14—C15—H15109.8
C3—N4—C21110.72 (11)C20—C15—H15109.8
C7—C2—N1108.82 (12)C2—C16—C23109.26 (11)
C7—C2—C16129.33 (12)C2—C16—C17108.93 (11)
N1—C2—C16121.80 (12)C23—C16—C17105.34 (11)
N4—C3—C14109.50 (12)C2—C16—C21108.70 (11)
N4—C3—H3A109.8C23—C16—C21115.68 (11)
C14—C3—H3A109.8C17—C16—C21108.74 (11)
N4—C3—H3B109.8C18—C17—C16113.48 (12)
C14—C3—H3B109.8C18—C17—H17A108.9
H3A—C3—H3B108.2C16—C17—H17A108.9
N4—C5—C6116.69 (12)C18—C17—H17B108.9
N4—C5—H5A108.1C16—C17—H17B108.9
C6—C5—H5A108.1H17A—C17—H17B107.7
N4—C5—H5B108.1C19—C18—C17110.25 (12)
C6—C5—H5B108.1C19—C18—H18A109.6
H5A—C5—H5B107.3C17—C18—H18A109.6
C7—C6—C5111.61 (12)C19—C18—H18B109.6
C7—C6—H6A109.3C17—C18—H18B109.6
C5—C6—H6A109.3H18A—C18—H18B108.1
C7—C6—H6B109.3C20—C19—C18123.64 (13)
C5—C6—H6B109.3C20—C19—H19118.2
H6A—C6—H6B108.0C18—C19—H19118.2
C2—C7—C8107.44 (12)C19—C20—C15120.65 (13)
C2—C7—C6127.05 (13)C19—C20—C21124.21 (13)
C8—C7—C6125.29 (13)C15—C20—C21115.03 (12)
C9—C8—C13119.11 (13)N4—C21—C20109.21 (11)
C9—C8—C7133.72 (14)N4—C21—C16113.89 (11)
C13—C8—C7107.18 (13)C20—C21—C16113.54 (11)
C10—C9—C8118.96 (15)N4—C21—H21106.6
C10—C9—H9120.5C20—C21—H21106.6
C8—C9—H9120.5C16—C21—H21106.6
C9—C10—C11121.12 (15)O1—C22—H22A109.5
C9—C10—H10119.4O1—C22—H22B109.5
C11—C10—H10119.4H22A—C22—H22B109.5
C12—C11—C10121.44 (14)O1—C22—H22C109.5
C12—C11—H11119.3H22A—C22—H22C109.5
C10—C11—H11119.3H22B—C22—H22C109.5
C11—C12—C13117.53 (15)O3—C23—O2123.37 (13)
C11—C12—H12121.2O3—C23—C16122.35 (12)
C13—C12—H12121.2O2—C23—C16114.20 (11)
N1—C13—C12130.87 (14)O2—C24—H24A109.5
N1—C13—C8107.29 (12)O2—C24—H24B109.5
C12—C13—C8121.84 (14)H24A—C24—H24B109.5
C15—C14—C3109.99 (12)O2—C24—H24C109.5
C15—C14—H14A109.7H24A—C24—H24C109.5
C3—C14—H14A109.7H24B—C24—H24C109.5
C15—C14—H14B109.7
C13—N1—C2—C70.53 (16)C7—C2—C16—C17146.69 (14)
C13—N1—C2—C16177.13 (12)N1—C2—C16—C1730.45 (17)
C5—N4—C3—C14166.45 (12)C7—C2—C16—C2128.35 (19)
C21—N4—C3—C1465.41 (15)N1—C2—C16—C21148.79 (12)
C3—N4—C5—C681.17 (15)C2—C16—C17—C18177.04 (11)
C21—N4—C5—C645.04 (16)C23—C16—C17—C1865.86 (14)
N4—C5—C6—C779.41 (15)C21—C16—C17—C1858.73 (15)
N1—C2—C7—C80.47 (15)C16—C17—C18—C1950.95 (16)
C16—C2—C7—C8176.97 (13)C17—C18—C19—C2019.8 (2)
N1—C2—C7—C6174.43 (13)C18—C19—C20—C15173.52 (13)
C16—C2—C7—C68.1 (2)C18—C19—C20—C212.4 (2)
C5—C6—C7—C224.9 (2)O1—C15—C20—C19106.75 (16)
C5—C6—C7—C8149.13 (13)C14—C15—C20—C19136.40 (15)
C2—C7—C8—C9180.00 (15)O1—C15—C20—C2169.54 (15)
C6—C7—C8—C95.0 (2)C14—C15—C20—C2147.31 (17)
C2—C7—C8—C130.24 (15)C5—N4—C21—C20175.36 (11)
C6—C7—C8—C13174.77 (13)C3—N4—C21—C2058.20 (14)
C13—C8—C9—C100.4 (2)C5—N4—C21—C1647.27 (15)
C7—C8—C9—C10179.88 (15)C3—N4—C21—C16173.71 (11)
C8—C9—C10—C110.4 (2)C19—C20—C21—N4134.12 (14)
C9—C10—C11—C120.9 (2)C15—C20—C21—N449.74 (15)
C10—C11—C12—C130.5 (2)C19—C20—C21—C165.84 (19)
C2—N1—C13—C12179.14 (14)C15—C20—C21—C16178.02 (12)
C2—N1—C13—C80.37 (15)C2—C16—C21—N481.24 (14)
C11—C12—C13—N1179.70 (14)C23—C16—C21—N442.06 (16)
C11—C12—C13—C80.3 (2)C17—C16—C21—N4160.30 (12)
C9—C8—C13—N1179.72 (12)C2—C16—C21—C20152.92 (11)
C7—C8—C13—N10.08 (15)C23—C16—C21—C2083.78 (14)
C9—C8—C13—C120.7 (2)C17—C16—C21—C2034.46 (15)
C7—C8—C13—C12179.48 (13)C24—O2—C23—O39.3 (2)
N4—C3—C14—C1561.07 (16)C24—O2—C23—C16173.83 (12)
C22—O1—C15—C14162.46 (12)C2—C16—C23—O339.04 (18)
C22—O1—C15—C2077.17 (15)C17—C16—C23—O377.84 (16)
C3—C14—C15—O168.38 (14)C21—C16—C23—O3162.05 (12)
C3—C14—C15—C2051.41 (17)C2—C16—C23—O2144.01 (12)
C7—C2—C16—C2398.72 (16)C17—C16—C23—O299.11 (13)
N1—C2—C16—C2384.13 (16)C21—C16—C23—O220.99 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.859 (17)2.187 (16)2.9759 (18)152.6 (15)
Symmetry code: (i) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC22H26N2O3
Mr366.45
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)6.914 (3), 11.232 (4), 11.806 (4)
α, β, γ (°)91.079 (6), 100.737 (5), 96.317 (6)
V3)894.5 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.43 × 0.23 × 0.13
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8672, 4028, 2868
Rint0.030
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.089, 1.00
No. of reflections4028
No. of parameters250
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.19

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.859 (17)2.187 (16)2.9759 (18)152.6 (15)
Symmetry code: (i) x+2, y+1, z+1.
 

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (2107298, 81001592) and the Natural Science Foundation of th Education Committee of Anhui Province (KJ2010A210).

References

First citationDanieli, B., Lesma, G., Luzzani, M., Passarella, D. & Silvani, A. (1977b). Tetrahedron, 34, 11291–11296.
First citationDanieli, B., Lesma, G., Martinelli, M., Passarella, D. & Silvani, A. (1977a). J. Org. Chem. 19, 6519–6523.
First citationKanfan, C., Massiot, G., Ahond, A., Das, B. C., Husson, H. P. & Potier, P. (1974). J. Chem. Soc. Chem Commun. pp. 164–165.
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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