15-Meth­oxy-14,15-di­hydro­andranginine

Wang, D.-L.; Cai, X.-H.; Huang, P.; Huang, H.-P.

doi:10.1107/S1600536813011604

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o833

doi:10.1107/S1600536813011604

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15-Methoxy-14,15-dihydroandranginine

Dian-Lei Wang,^a Xiang-Hai Cai,^b Peng Huang ^a ^* and He-Ping Huang ^a ^*

^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 ). For the structures of related compounds, see: Danieli et al. (1977a ) and for applications of similar compounds see: Danieli et al. (1977a,b )

Experimental

Crystal data

C₂₂H₂₆N₂O₃
M_r = 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)
R_int = 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
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813011604/ld2092sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813011604/ld2092Isup2.hkl

checkCIF report

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.

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

	Fig. 1. : The molecular structure of the title molecule(I) with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. : packing diagram of (I). Hydrogen bonds shown as dashed lines.

15-Methoxy-14,15-dihydroandranginine top

Crystal data top

C₂₂H₂₆N₂O₃	Z = 2
M_r = 366.45	F(000) = 392
Triclinic, P1	D_x = 1.361 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.914 (3) Å	Cell parameters from 2653 reflections
b = 11.232 (4) Å	θ = 3.0–27.5°
c = 11.806 (4) Å	µ = 0.09 mm⁻¹
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 Anode	R_int = 0.030
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
Detector resolution: 28.5714 pixels mm^-1	h = −8→8
phi and ω scans	k = −14→14
8672 measured reflections	l = −14→15
4028 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0318P)² + 0.160P] where P = (F_o² + 2F_c²)/3
4028 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₂₆N₂O₃	γ = 96.317 (6)°
M_r = 366.45	V = 894.5 (6) Å³
Triclinic, P1	Z = 2
a = 6.914 (3) Å	Mo Kα radiation
b = 11.232 (4) Å	µ = 0.09 mm⁻¹
c = 11.806 (4) Å	T = 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 reflections	R_int = 0.030
4028 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.27 e Å⁻³
4028 reflections	Δρ_min = −0.19 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	0.60683 (16)	0.85999 (9)	0.01190 (9)	0.0277 (3)
O2	0.46541 (15)	0.48350 (9)	0.27560 (8)	0.0239 (2)
O3	0.67895 (15)	0.46849 (9)	0.44057 (8)	0.0244 (2)
N1	1.00622 (18)	0.69322 (12)	0.50300 (10)	0.0205 (3)
N4	0.42553 (17)	0.72717 (10)	0.24809 (9)	0.0185 (3)
C2	0.8300 (2)	0.71262 (13)	0.43152 (11)	0.0175 (3)
C3	0.3346 (2)	0.81220 (14)	0.16762 (12)	0.0229 (3)
H3A	0.4208	0.8895	0.1758	0.028*
H3B	0.2048	0.8269	0.1856	0.028*
C5	0.4122 (2)	0.75869 (13)	0.36721 (11)	0.0194 (3)
H5A	0.4215	0.6854	0.4123	0.023*
H5B	0.2793	0.7840	0.3669	0.023*
C6	0.5671 (2)	0.85711 (13)	0.43018 (12)	0.0215 (3)
H6A	0.5876	0.9223	0.3769	0.026*
H6B	0.5176	0.8911	0.4959	0.026*
C7	0.7607 (2)	0.81020 (13)	0.47397 (12)	0.0189 (3)
C8	0.8993 (2)	0.85448 (13)	0.57542 (12)	0.0201 (3)
C9	0.9085 (2)	0.95044 (14)	0.65452 (12)	0.0246 (3)
H9	0.8069	1.0019	0.6457	0.030*
C10	1.0671 (2)	0.96896 (14)	0.74531 (13)	0.0275 (4)
H10	1.0739	1.0336	0.7996	0.033*
C11	1.2176 (2)	0.89460 (14)	0.75890 (13)	0.0280 (4)
H11	1.3261	0.9102	0.8217	0.034*
C12	1.2125 (2)	0.79874 (14)	0.68306 (12)	0.0262 (4)
H12	1.3149	0.7478	0.6929	0.031*
C13	1.0515 (2)	0.77946 (13)	0.59135 (12)	0.0202 (3)
C14	0.3065 (2)	0.76125 (15)	0.04513 (12)	0.0259 (4)
H14A	0.2199	0.6841	0.0371	0.031*
H14B	0.2414	0.8173	−0.0092	0.031*
C15	0.5046 (2)	0.74198 (14)	0.01609 (12)	0.0235 (3)
H15	0.4846	0.6994	−0.0611	0.028*
C16	0.7451 (2)	0.63502 (12)	0.32228 (11)	0.0168 (3)
C17	0.9184 (2)	0.59056 (13)	0.27308 (12)	0.0214 (3)
H17A	1.0106	0.6608	0.2605	0.026*
H17B	0.9920	0.5411	0.3308	0.026*
C18	0.8514 (2)	0.51737 (14)	0.16040 (12)	0.0242 (3)
H18A	0.9685	0.5019	0.1276	0.029*
H18B	0.7812	0.4392	0.1750	0.029*
C19	0.7168 (2)	0.58305 (13)	0.07633 (12)	0.0231 (3)
H19	0.6987	0.5606	−0.0033	0.028*
C20	0.6212 (2)	0.67091 (13)	0.10661 (12)	0.0200 (3)
C21	0.6292 (2)	0.71353 (12)	0.23085 (11)	0.0177 (3)
H21	0.7039	0.7957	0.2404	0.021*
C22	0.7679 (3)	0.86269 (17)	−0.04602 (15)	0.0386 (4)
H22A	0.8327	0.9450	−0.0440	0.046*
H22B	0.7199	0.8342	−0.1264	0.046*
H22C	0.8632	0.8107	−0.0079	0.046*
C23	0.6256 (2)	0.52135 (12)	0.35387 (12)	0.0174 (3)
C24	0.3361 (2)	0.38405 (13)	0.30607 (13)	0.0250 (3)
H24A	0.2227	0.3645	0.2427	0.030*
H24B	0.2888	0.4061	0.3760	0.030*
H24C	0.4092	0.3142	0.3202	0.030*
H1N	1.078 (2)	0.6370 (16)	0.4959 (14)	0.032 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0297 (6)	0.0267 (6)	0.0277 (6)	0.0001 (5)	0.0091 (5)	0.0057 (5)
O2	0.0229 (6)	0.0209 (6)	0.0248 (6)	−0.0055 (4)	0.0007 (5)	0.0038 (4)
O3	0.0259 (6)	0.0219 (6)	0.0249 (6)	0.0035 (4)	0.0028 (5)	0.0062 (4)
N1	0.0180 (7)	0.0223 (7)	0.0209 (7)	0.0044 (5)	0.0020 (5)	0.0000 (5)
N4	0.0168 (6)	0.0219 (7)	0.0172 (6)	0.0036 (5)	0.0031 (5)	0.0027 (5)
C2	0.0161 (7)	0.0182 (7)	0.0174 (7)	−0.0001 (6)	0.0020 (6)	0.0035 (6)
C3	0.0193 (8)	0.0253 (8)	0.0249 (8)	0.0061 (6)	0.0035 (6)	0.0064 (6)
C5	0.0181 (7)	0.0198 (8)	0.0211 (7)	0.0036 (6)	0.0052 (6)	0.0018 (6)
C6	0.0225 (8)	0.0188 (8)	0.0232 (8)	0.0039 (6)	0.0036 (6)	−0.0007 (6)
C7	0.0196 (7)	0.0170 (7)	0.0194 (7)	0.0000 (6)	0.0032 (6)	0.0018 (6)
C8	0.0215 (8)	0.0205 (8)	0.0175 (7)	−0.0021 (6)	0.0039 (6)	0.0021 (6)
C9	0.0278 (9)	0.0212 (8)	0.0243 (8)	−0.0013 (6)	0.0063 (7)	−0.0001 (6)
C10	0.0338 (9)	0.0250 (8)	0.0213 (8)	−0.0062 (7)	0.0050 (7)	−0.0028 (6)
C11	0.0268 (9)	0.0341 (9)	0.0183 (8)	−0.0078 (7)	−0.0016 (7)	0.0023 (7)
C12	0.0217 (8)	0.0311 (9)	0.0244 (8)	0.0006 (7)	0.0017 (7)	0.0042 (7)
C13	0.0203 (8)	0.0209 (8)	0.0188 (7)	−0.0016 (6)	0.0045 (6)	0.0015 (6)
C14	0.0218 (8)	0.0328 (9)	0.0216 (8)	0.0025 (7)	0.0003 (6)	0.0063 (7)
C15	0.0237 (8)	0.0266 (8)	0.0190 (7)	−0.0003 (6)	0.0030 (6)	0.0014 (6)
C16	0.0164 (7)	0.0161 (7)	0.0176 (7)	0.0021 (6)	0.0030 (6)	0.0007 (5)
C17	0.0178 (7)	0.0238 (8)	0.0226 (8)	0.0022 (6)	0.0038 (6)	0.0012 (6)
C18	0.0245 (8)	0.0246 (8)	0.0250 (8)	0.0036 (6)	0.0084 (7)	−0.0023 (6)
C19	0.0245 (8)	0.0267 (8)	0.0178 (7)	−0.0008 (6)	0.0054 (6)	−0.0023 (6)
C20	0.0174 (7)	0.0223 (8)	0.0190 (7)	−0.0031 (6)	0.0035 (6)	0.0002 (6)
C21	0.0169 (7)	0.0160 (7)	0.0199 (7)	0.0009 (6)	0.0033 (6)	0.0021 (6)
C22	0.0347 (10)	0.0414 (11)	0.0410 (10)	−0.0059 (8)	0.0162 (8)	0.0048 (8)
C23	0.0176 (7)	0.0160 (7)	0.0200 (7)	0.0048 (6)	0.0061 (6)	−0.0011 (6)
C24	0.0223 (8)	0.0193 (8)	0.0332 (9)	−0.0031 (6)	0.0083 (7)	0.0009 (6)

Geometric parameters (Å, º) top

O1—C22	1.4091 (19)	C11—C12	1.381 (2)
O1—C15	1.4381 (18)	C11—H11	0.9500
O2—C23	1.3274 (17)	C12—C13	1.396 (2)
O2—C24	1.4461 (17)	C12—H12	0.9500
O3—C23	1.2109 (16)	C14—C15	1.509 (2)
N1—C13	1.3775 (19)	C14—H14A	0.9900
N1—C2	1.3881 (18)	C14—H14B	0.9900
N1—H1N	0.859 (17)	C15—C20	1.5105 (19)
N4—C5	1.4657 (18)	C15—H15	1.0000
N4—C3	1.4675 (17)	C16—C23	1.5337 (19)
N4—C21	1.4836 (18)	C16—C17	1.549 (2)
C2—C7	1.366 (2)	C16—C21	1.5665 (18)
C2—C16	1.5265 (19)	C17—C18	1.518 (2)
C3—C14	1.515 (2)	C17—H17A	0.9900
C3—H3A	0.9900	C17—H17B	0.9900
C3—H3B	0.9900	C18—C19	1.493 (2)
C5—C6	1.527 (2)	C18—H18A	0.9900
C5—H5A	0.9900	C18—H18B	0.9900
C5—H5B	0.9900	C19—C20	1.325 (2)
C6—C7	1.498 (2)	C19—H19	0.9500
C6—H6A	0.9900	C20—C21	1.523 (2)
C6—H6B	0.9900	C21—H21	1.0000
C7—C8	1.430 (2)	C22—H22A	0.9800
C8—C9	1.401 (2)	C22—H22B	0.9800
C8—C13	1.407 (2)	C22—H22C	0.9800
C9—C10	1.378 (2)	C24—H24A	0.9800
C9—H9	0.9500	C24—H24B	0.9800
C10—C11	1.393 (2)	C24—H24C	0.9800
C10—H10	0.9500

C22—O1—C15	113.67 (12)	C3—C14—H14B	109.7
C23—O2—C24	116.57 (11)	H14A—C14—H14B	108.2
C13—N1—C2	109.27 (12)	O1—C15—C14	105.53 (12)
C13—N1—H1N	123.4 (11)	O1—C15—C20	110.41 (12)
C2—N1—H1N	127.3 (11)	C14—C15—C20	111.29 (12)
C5—N4—C3	111.16 (11)	O1—C15—H15	109.8
C5—N4—C21	114.27 (10)	C14—C15—H15	109.8
C3—N4—C21	110.72 (11)	C20—C15—H15	109.8
C7—C2—N1	108.82 (12)	C2—C16—C23	109.26 (11)
C7—C2—C16	129.33 (12)	C2—C16—C17	108.93 (11)
N1—C2—C16	121.80 (12)	C23—C16—C17	105.34 (11)
N4—C3—C14	109.50 (12)	C2—C16—C21	108.70 (11)
N4—C3—H3A	109.8	C23—C16—C21	115.68 (11)
C14—C3—H3A	109.8	C17—C16—C21	108.74 (11)
N4—C3—H3B	109.8	C18—C17—C16	113.48 (12)
C14—C3—H3B	109.8	C18—C17—H17A	108.9
H3A—C3—H3B	108.2	C16—C17—H17A	108.9
N4—C5—C6	116.69 (12)	C18—C17—H17B	108.9
N4—C5—H5A	108.1	C16—C17—H17B	108.9
C6—C5—H5A	108.1	H17A—C17—H17B	107.7
N4—C5—H5B	108.1	C19—C18—C17	110.25 (12)
C6—C5—H5B	108.1	C19—C18—H18A	109.6
H5A—C5—H5B	107.3	C17—C18—H18A	109.6
C7—C6—C5	111.61 (12)	C19—C18—H18B	109.6
C7—C6—H6A	109.3	C17—C18—H18B	109.6
C5—C6—H6A	109.3	H18A—C18—H18B	108.1
C7—C6—H6B	109.3	C20—C19—C18	123.64 (13)
C5—C6—H6B	109.3	C20—C19—H19	118.2
H6A—C6—H6B	108.0	C18—C19—H19	118.2
C2—C7—C8	107.44 (12)	C19—C20—C15	120.65 (13)
C2—C7—C6	127.05 (13)	C19—C20—C21	124.21 (13)
C8—C7—C6	125.29 (13)	C15—C20—C21	115.03 (12)
C9—C8—C13	119.11 (13)	N4—C21—C20	109.21 (11)
C9—C8—C7	133.72 (14)	N4—C21—C16	113.89 (11)
C13—C8—C7	107.18 (13)	C20—C21—C16	113.54 (11)
C10—C9—C8	118.96 (15)	N4—C21—H21	106.6
C10—C9—H9	120.5	C20—C21—H21	106.6
C8—C9—H9	120.5	C16—C21—H21	106.6
C9—C10—C11	121.12 (15)	O1—C22—H22A	109.5
C9—C10—H10	119.4	O1—C22—H22B	109.5
C11—C10—H10	119.4	H22A—C22—H22B	109.5
C12—C11—C10	121.44 (14)	O1—C22—H22C	109.5
C12—C11—H11	119.3	H22A—C22—H22C	109.5
C10—C11—H11	119.3	H22B—C22—H22C	109.5
C11—C12—C13	117.53 (15)	O3—C23—O2	123.37 (13)
C11—C12—H12	121.2	O3—C23—C16	122.35 (12)
C13—C12—H12	121.2	O2—C23—C16	114.20 (11)
N1—C13—C12	130.87 (14)	O2—C24—H24A	109.5
N1—C13—C8	107.29 (12)	O2—C24—H24B	109.5
C12—C13—C8	121.84 (14)	H24A—C24—H24B	109.5
C15—C14—C3	109.99 (12)	O2—C24—H24C	109.5
C15—C14—H14A	109.7	H24A—C24—H24C	109.5
C3—C14—H14A	109.7	H24B—C24—H24C	109.5
C15—C14—H14B	109.7

C13—N1—C2—C7	−0.53 (16)	C7—C2—C16—C17	146.69 (14)
C13—N1—C2—C16	177.13 (12)	N1—C2—C16—C17	−30.45 (17)
C5—N4—C3—C14	−166.45 (12)	C7—C2—C16—C21	28.35 (19)
C21—N4—C3—C14	65.41 (15)	N1—C2—C16—C21	−148.79 (12)
C3—N4—C5—C6	−81.17 (15)	C2—C16—C17—C18	−177.04 (11)
C21—N4—C5—C6	45.04 (16)	C23—C16—C17—C18	65.86 (14)
N4—C5—C6—C7	−79.41 (15)	C21—C16—C17—C18	−58.73 (15)
N1—C2—C7—C8	0.47 (15)	C16—C17—C18—C19	50.95 (16)
C16—C2—C7—C8	−176.97 (13)	C17—C18—C19—C20	−19.8 (2)
N1—C2—C7—C6	−174.43 (13)	C18—C19—C20—C15	173.52 (13)
C16—C2—C7—C6	8.1 (2)	C18—C19—C20—C21	−2.4 (2)
C5—C6—C7—C2	24.9 (2)	O1—C15—C20—C19	−106.75 (16)
C5—C6—C7—C8	−149.13 (13)	C14—C15—C20—C19	136.40 (15)
C2—C7—C8—C9	180.00 (15)	O1—C15—C20—C21	69.54 (15)
C6—C7—C8—C9	−5.0 (2)	C14—C15—C20—C21	−47.31 (17)
C2—C7—C8—C13	−0.24 (15)	C5—N4—C21—C20	175.36 (11)
C6—C7—C8—C13	174.77 (13)	C3—N4—C21—C20	−58.20 (14)
C13—C8—C9—C10	0.4 (2)	C5—N4—C21—C16	47.27 (15)
C7—C8—C9—C10	−179.88 (15)	C3—N4—C21—C16	173.71 (11)
C8—C9—C10—C11	0.4 (2)	C19—C20—C21—N4	−134.12 (14)
C9—C10—C11—C12	−0.9 (2)	C15—C20—C21—N4	49.74 (15)
C10—C11—C12—C13	0.5 (2)	C19—C20—C21—C16	−5.84 (19)
C2—N1—C13—C12	−179.14 (14)	C15—C20—C21—C16	178.02 (12)
C2—N1—C13—C8	0.37 (15)	C2—C16—C21—N4	−81.24 (14)
C11—C12—C13—N1	179.70 (14)	C23—C16—C21—N4	42.06 (16)
C11—C12—C13—C8	0.3 (2)	C17—C16—C21—N4	160.30 (12)
C9—C8—C13—N1	179.72 (12)	C2—C16—C21—C20	152.92 (11)
C7—C8—C13—N1	−0.08 (15)	C23—C16—C21—C20	−83.78 (14)
C9—C8—C13—C12	−0.7 (2)	C17—C16—C21—C20	34.46 (15)
C7—C8—C13—C12	179.48 (13)	C24—O2—C23—O3	9.3 (2)
N4—C3—C14—C15	−61.07 (16)	C24—O2—C23—C16	−173.83 (12)
C22—O1—C15—C14	−162.46 (12)	C2—C16—C23—O3	−39.04 (18)
C22—O1—C15—C20	77.17 (15)	C17—C16—C23—O3	77.84 (16)
C3—C14—C15—O1	−68.38 (14)	C21—C16—C23—O3	−162.05 (12)
C3—C14—C15—C20	51.41 (17)	C2—C16—C23—O2	144.01 (12)
C7—C2—C16—C23	−98.72 (16)	C17—C16—C23—O2	−99.11 (13)
N1—C2—C16—C23	84.13 (16)	C21—C16—C23—O2	20.99 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆N₂O₃
M_r	366.45
Crystal system, space group	Triclinic, 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)
V (Å³)	894.5 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.23 × 0.13

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8672, 4028, 2868
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.089, 1.00
No. of reflections	4028
No. of parameters	250
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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.

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

Danieli, B., Lesma, G., Luzzani, M., Passarella, D. & Silvani, A. (1977b). Tetrahedron, 34, 11291–11296. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar