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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Di­hydro­allocryptopine

aCollege of Science, Northwest Agriculture and Forestry University, Yangling 712100, People's Republic of China
*Correspondence e-mail: zhoulechem@yahoo.com.cn

(Received 12 November 2011; accepted 3 December 2011; online 10 December 2011)

In the title compound [systematic name: 7,8-dimeth­oxy-11-methyl-17,19-dioxa-11-aza­tetra­cyclo­[12.7.0.04,9.016,20]henicosa-1(21),4,6,8,14,16 (20)-hexaen-2-ol], C21H25NO5, the benzene rings are inclined at a dihedral angle of 23.16 (5)°. One of the meth­oxy C atoms is close to coplanar with its attached ring [deviation = 0.129 (3) Å], whereas the other is orientated away from the ring [deviation = −1.124 (2) Å]. The 10-membered ring is highly puckered, and the OH and CH3 substituents project to the same side of the ring. In the crystal, O—H⋯O hydrogen bonds link the mol­ecules into [010] chains and C—H⋯O and C—H⋯π inter­actions consolidate the packing.

Related literature

For the synthesis of the title compound, see: Wada et al. (2007[Wada, Y., Kaga, H., Uchiito, S., Kumazawa, E., Tomiki, M., Onozaki, Y., Kurono, N., Tokuda, M., Ohkuma, T. & Orit, K. (2007). J. Org. Chem. 72, 7301-7306.]). For the biological activity of allocryptopine derivatives, see: Morteza et al. (2003[Morteza, K., Amin, G., Shidfar, M. R., Hadizadeh, H. & Shafiee, A. (2003). Fitoterapia, 74, 493-496.]); Yan et al. (2009[Yan, M., Sun, J. H., Lu, Z. Q., Chen, G. T., Guan, S. H., Liu, X., Jiang, B. H., Ye, M. & Guo, D. A. (2009). J. Chromatogr. A, 1216, 2045-2062.]); Capasso et al. (1997[Capasso, A., Piacente, S. & Pizza, C. (1997). Planta Med. 63, 326-328.]); Jeong et al. (2009[Jeong, E. J., Ma, C. J., Lee, K. Y., Kim, S. H., Sung, S. H. & Kim, Y. C. (2009). J. Ethnopharmacol. 121, 98-105.]); Zhao et al. (2008[Zhao, G., Jiang, Z. H., Zheng, X. W., Zang, S. Y. & Guo, L. H. (2008). Pharmacol. Biochem. Behav. 90, 363-371.]). For a related structure, see: Valpuesta et al. (2006[Valpuesta, M., Diaz, A., Suau, R. & Torres, G. (2006). Eur. J. Org. Chem. pp. 964-971.]).

[Scheme 1]

Experimental

Crystal data
  • C21H25NO5

  • Mr = 371.42

  • Monoclinic, P 21 /c

  • a = 14.2557 (19) Å

  • b = 9.3705 (13) Å

  • c = 15.278 (2) Å

  • β = 106.601 (2)°

  • V = 1955.8 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.45 × 0.24 × 0.21 mm

Data collection
  • Bruker SMART APEX II CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.961, Tmax = 0.981

  • 14189 measured reflections

  • 3646 independent reflections

  • 2766 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.110

  • S = 1.02

  • 3646 reflections

  • 248 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O5i 0.82 2.03 2.8380 (16) 168
C7—H7A⋯O4ii 0.97 2.57 3.405 (3) 144
C18—H18⋯O3iii 0.93 2.53 3.229 (2) 132
C7—H7BCg2iv 0.97 2.57 3.464 (3) 153
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, z; (iii) -x, -y, -z; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. 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: 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 allocryptopine derivatives have recently attracted great attention due to their antifungal activity (Morteza et al. 2003), antibacterial activity (Yan et al. 2009), analgesic effect (Capasso et al. 1997), anti-dementia (Jeong et al. 2009; Zhao et al. 2008), and so on. With the interests in the synthesis of allocryptopine derivatives with biological activity, we report here the synthesis and crystal structure of the title compound, (I).

As shown in Fig. 1, the molecule of the title compound is characterized by the presence of a ten-membered ring (hexahydrodibenzo[c,g]azecine) with a methylated tertiary nitrogen atom and a hydroxyl group fused to two aryl moieties. In general, the title compound have two oxygenated substituents on the benzene ring and two methoxyl on the other benzene ring. Benzene rings C1/C2/C3/C4/C5/C6 and C10/C11/C16/C17/C18/C19 are inclined with respect to one another with a dihedral angle of 23.16 (5)°.

In the crystal structure, two adjacent molecules are linked by weak intermolecular O—H···O or C—H···O hydrogen bond into a one-dimension chain along b axis. These chains are further connected by C—H···π interaction into two-dimension sheets.

Related literature top

For the synthesis of the title compound, see: Wada et al. (2007). For the biological activity of allocryptopine derivatives, see: Morteza et al. (2003); Yan et al. (2009); Capasso et al. (1997); Jeong et al. (2009); Zhao et al. (2008). For related literature [on what subject?], see: Valpuesta et al. (2006).

Experimental top

The title compound was synthesized according to the literature procedure (Wada et al. 2007), and colourless blocks of (I) were obtained from a solution in methanol by slow evaporation at room temperature.

Refinement top

H atoms were positioned geometrically and treated as riding, with C—H bond lengths constrained to 0.93 (aromatic CH), or 0.97 Å (methylene CH2), or 0.96Å (methyl CH3), and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Uceq(O).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (50% displacement ellipsoids).
[Figure 2] Fig. 2. The two-dimension sheet structure of the title compound.
7,8-dimethoxy-11-methyl-17,19-dioxa-11- azatetracyclo[12.7.0.04,9.016,20]henicosa-1(21),4,6,8,14,16 (20)-hexaen-2-ol top
Crystal data top
C21H25NO5F(000) = 792
Mr = 371.42Dx = 1.261 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.2557 (19) ÅCell parameters from 3665 reflections
b = 9.3705 (13) Åθ = 2.6–22.6°
c = 15.278 (2) ŵ = 0.09 mm1
β = 106.601 (2)°T = 296 K
V = 1955.8 (5) Å3Block, colourless
Z = 40.45 × 0.24 × 0.21 mm
Data collection top
Bruker SMART APEX II CCD
diffractometer
3646 independent reflections
Radiation source: fine-focus sealed tube2766 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
phi and ω scansθmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1717
Tmin = 0.961, Tmax = 0.981k = 1111
14189 measured reflectionsl = 1818
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) = 0.110H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0526P)2 + 0.4075P]
where P = (Fo2 + 2Fc2)/3
3646 reflections(Δ/σ)max = 0.001
248 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C21H25NO5V = 1955.8 (5) Å3
Mr = 371.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.2557 (19) ŵ = 0.09 mm1
b = 9.3705 (13) ÅT = 296 K
c = 15.278 (2) Å0.45 × 0.24 × 0.21 mm
β = 106.601 (2)°
Data collection top
Bruker SMART APEX II CCD
diffractometer
3646 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2766 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.981Rint = 0.026
14189 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.02Δρmax = 0.18 e Å3
3646 reflectionsΔρmin = 0.21 e Å3
248 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
C10.27622 (11)0.13752 (17)0.24521 (10)0.0402 (4)
C20.32459 (11)0.17612 (18)0.18061 (11)0.0460 (4)
H20.29540.16120.11860.055*
C30.41532 (12)0.2359 (2)0.21064 (13)0.0528 (4)
C40.46009 (13)0.2568 (2)0.30202 (14)0.0592 (5)
C50.41615 (12)0.2188 (2)0.36684 (13)0.0588 (5)
H50.44780.23290.42850.071*
C60.32187 (11)0.15767 (19)0.33900 (11)0.0464 (4)
C70.55723 (15)0.3447 (3)0.22467 (16)0.0776 (6)
H7A0.61860.31060.21680.093*
H7B0.55390.44710.21510.093*
C80.17251 (11)0.08232 (16)0.20842 (9)0.0375 (3)
H80.15450.02800.25600.045*
C90.10207 (11)0.20855 (17)0.17812 (11)0.0410 (4)
H9A0.12340.28500.22210.049*
H9B0.10790.24290.12000.049*
C100.00464 (11)0.17974 (16)0.16778 (10)0.0381 (3)
C110.04578 (11)0.20517 (16)0.23982 (10)0.0381 (3)
C120.01951 (11)0.25595 (18)0.33146 (11)0.0444 (4)
H12A0.04770.34790.32430.053*
H12B0.01890.26700.37420.053*
C130.19042 (11)0.2073 (2)0.42234 (11)0.0507 (4)
H13A0.19020.20990.48570.061*
H13B0.19880.30420.40350.061*
C140.27663 (12)0.1155 (2)0.41377 (11)0.0530 (5)
H14A0.32740.11830.47170.064*
H14B0.25440.01740.40340.064*
C150.06335 (14)0.0326 (2)0.40923 (13)0.0650 (5)
H15A0.11370.03880.42550.098*
H15B0.00590.00730.36720.098*
H15C0.04780.06460.46310.098*
C160.14540 (11)0.18373 (17)0.22552 (10)0.0410 (4)
C170.20575 (11)0.13956 (18)0.14017 (11)0.0452 (4)
C180.16472 (12)0.11260 (18)0.07058 (11)0.0463 (4)
H180.20360.08090.01420.056*
C190.06541 (12)0.13279 (17)0.08482 (10)0.0430 (4)
H190.03850.11430.03720.052*
C200.22408 (15)0.0958 (2)0.33403 (14)0.0674 (5)
H20A0.26900.04190.28680.101*
H20B0.25690.12930.37690.101*
H20C0.17000.03610.36500.101*
C210.36808 (14)0.0889 (3)0.04815 (15)0.0854 (7)
H21A0.36460.15870.00320.128*
H21B0.43370.08460.05290.128*
H21C0.34980.00280.03030.128*
N10.09746 (9)0.15187 (14)0.36674 (8)0.0403 (3)
O10.55278 (10)0.3128 (2)0.31403 (11)0.0870 (5)
O20.47711 (10)0.27719 (17)0.16005 (10)0.0764 (4)
O30.16204 (8)0.00602 (12)0.12969 (7)0.0458 (3)
H30.17350.08920.14580.069*
O40.30345 (8)0.12764 (16)0.13363 (8)0.0642 (4)
O50.18857 (8)0.21548 (12)0.29420 (7)0.0497 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0378 (8)0.0418 (9)0.0418 (9)0.0010 (7)0.0127 (7)0.0015 (7)
C20.0419 (9)0.0530 (10)0.0431 (9)0.0002 (7)0.0121 (7)0.0017 (7)
C30.0446 (10)0.0587 (11)0.0594 (11)0.0037 (8)0.0216 (8)0.0003 (9)
C40.0407 (9)0.0668 (12)0.0694 (12)0.0113 (9)0.0147 (9)0.0111 (10)
C50.0432 (10)0.0793 (14)0.0511 (10)0.0077 (9)0.0089 (8)0.0145 (9)
C60.0395 (9)0.0553 (10)0.0428 (9)0.0013 (7)0.0091 (7)0.0051 (8)
C70.0530 (12)0.0853 (16)0.0995 (17)0.0185 (11)0.0298 (12)0.0081 (13)
C80.0417 (8)0.0422 (9)0.0301 (7)0.0026 (7)0.0125 (6)0.0025 (6)
C90.0429 (9)0.0425 (9)0.0389 (8)0.0011 (7)0.0140 (7)0.0029 (7)
C100.0408 (8)0.0357 (8)0.0375 (8)0.0027 (6)0.0111 (6)0.0027 (6)
C110.0407 (8)0.0346 (8)0.0381 (8)0.0007 (6)0.0095 (7)0.0015 (6)
C120.0430 (9)0.0473 (9)0.0436 (9)0.0029 (7)0.0136 (7)0.0117 (7)
C130.0456 (9)0.0690 (12)0.0369 (8)0.0084 (8)0.0108 (7)0.0137 (8)
C140.0440 (9)0.0768 (13)0.0347 (8)0.0011 (9)0.0057 (7)0.0011 (8)
C150.0613 (11)0.0714 (13)0.0612 (12)0.0116 (10)0.0156 (9)0.0148 (10)
C160.0408 (8)0.0424 (9)0.0413 (9)0.0025 (7)0.0142 (7)0.0021 (7)
C170.0376 (9)0.0493 (10)0.0456 (9)0.0016 (7)0.0069 (7)0.0019 (7)
C180.0458 (9)0.0531 (10)0.0350 (8)0.0012 (8)0.0036 (7)0.0040 (7)
C190.0478 (9)0.0462 (9)0.0357 (8)0.0048 (7)0.0130 (7)0.0005 (7)
C200.0694 (13)0.0749 (14)0.0672 (12)0.0005 (11)0.0347 (10)0.0095 (10)
C210.0436 (11)0.128 (2)0.0719 (14)0.0027 (12)0.0039 (10)0.0165 (14)
N10.0398 (7)0.0478 (8)0.0326 (6)0.0057 (6)0.0095 (5)0.0040 (6)
O10.0522 (8)0.1244 (14)0.0852 (11)0.0369 (9)0.0208 (7)0.0178 (10)
O20.0563 (8)0.1040 (12)0.0760 (9)0.0229 (8)0.0303 (7)0.0018 (8)
O30.0541 (7)0.0482 (7)0.0363 (6)0.0031 (6)0.0150 (5)0.0074 (5)
O40.0363 (6)0.0958 (10)0.0561 (7)0.0040 (6)0.0062 (5)0.0098 (7)
O50.0496 (7)0.0551 (7)0.0499 (7)0.0007 (5)0.0229 (5)0.0060 (5)
Geometric parameters (Å, º) top
C1—C21.403 (2)C12—H12B0.9700
C1—C61.407 (2)C13—N11.4506 (19)
C1—C81.515 (2)C13—C141.536 (2)
C2—C31.363 (2)C13—H13A0.9700
C2—H20.9300C13—H13B0.9700
C3—C41.373 (3)C14—H14A0.9700
C3—O21.383 (2)C14—H14B0.9700
C4—C51.362 (3)C15—N11.445 (2)
C4—O11.384 (2)C15—H15A0.9600
C5—C61.410 (2)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C6—C141.516 (2)C16—O51.3920 (18)
C7—O11.417 (3)C16—C171.404 (2)
C7—O21.427 (2)C17—O41.3720 (19)
C7—H7A0.9700C17—C181.375 (2)
C7—H7B0.9700C18—C191.383 (2)
C8—O31.4323 (17)C18—H180.9300
C8—C91.535 (2)C19—H190.9300
C8—H80.9800C20—O51.435 (2)
C9—C101.508 (2)C20—H20A0.9600
C9—H9A0.9700C20—H20B0.9600
C9—H9B0.9700C20—H20C0.9600
C10—C191.387 (2)C21—O41.414 (2)
C10—C111.407 (2)C21—H21A0.9600
C11—C161.388 (2)C21—H21B0.9600
C11—C121.519 (2)C21—H21C0.9600
C12—N11.461 (2)O3—H30.8200
C12—H12A0.9700
C2—C1—C6120.30 (14)N1—C13—H13A109.3
C2—C1—C8116.79 (13)C14—C13—H13A109.3
C6—C1—C8122.82 (13)N1—C13—H13B109.3
C3—C2—C1118.61 (15)C14—C13—H13B109.3
C3—C2—H2120.7H13A—C13—H13B108.0
C1—C2—H2120.7C6—C14—C13116.17 (15)
C2—C3—C4121.44 (16)C6—C14—H14A108.2
C2—C3—O2128.43 (17)C13—C14—H14A108.2
C4—C3—O2110.06 (15)C6—C14—H14B108.2
C5—C4—C3121.68 (16)C13—C14—H14B108.2
C5—C4—O1128.52 (18)H14A—C14—H14B107.4
C3—C4—O1109.74 (17)N1—C15—H15A109.5
C4—C5—C6118.93 (16)N1—C15—H15B109.5
C4—C5—H5120.5H15A—C15—H15B109.5
C6—C5—H5120.5N1—C15—H15C109.5
C1—C6—C5119.03 (15)H15A—C15—H15C109.5
C1—C6—C14124.04 (14)H15B—C15—H15C109.5
C5—C6—C14116.92 (14)C11—C16—O5120.21 (13)
O1—C7—O2109.03 (15)C11—C16—C17121.11 (14)
O1—C7—H7A109.9O5—C16—C17118.53 (13)
O2—C7—H7A109.9O4—C17—C18125.15 (14)
O1—C7—H7B109.9O4—C17—C16115.57 (14)
O2—C7—H7B109.9C18—C17—C16119.28 (14)
H7A—C7—H7B108.3C17—C18—C19119.72 (14)
O3—C8—C1111.43 (12)C17—C18—H18120.1
O3—C8—C9106.85 (12)C19—C18—H18120.1
C1—C8—C9109.50 (13)C18—C19—C10122.10 (14)
O3—C8—H8109.7C18—C19—H19118.9
C1—C8—H8109.7C10—C19—H19118.9
C9—C8—H8109.7O5—C20—H20A109.5
C10—C9—C8116.55 (13)O5—C20—H20B109.5
C10—C9—H9A108.2H20A—C20—H20B109.5
C8—C9—H9A108.2O5—C20—H20C109.5
C10—C9—H9B108.2H20A—C20—H20C109.5
C8—C9—H9B108.2H20B—C20—H20C109.5
H9A—C9—H9B107.3O4—C21—H21A109.5
C19—C10—C11118.51 (14)O4—C21—H21B109.5
C19—C10—C9120.04 (13)H21A—C21—H21B109.5
C11—C10—C9121.40 (13)O4—C21—H21C109.5
C16—C11—C10119.24 (13)H21A—C21—H21C109.5
C16—C11—C12121.34 (13)H21B—C21—H21C109.5
C10—C11—C12119.42 (13)C15—N1—C13112.48 (14)
N1—C12—C11109.40 (12)C15—N1—C12111.35 (14)
N1—C12—H12A109.8C13—N1—C12116.64 (13)
C11—C12—H12A109.8C4—O1—C7104.83 (15)
N1—C12—H12B109.8C3—O2—C7104.43 (15)
C11—C12—H12B109.8C8—O3—H3109.5
H12A—C12—H12B108.2C17—O4—C21117.92 (14)
N1—C13—C14111.64 (14)C16—O5—C20115.97 (13)
C6—C1—C2—C31.3 (2)C1—C6—C14—C1371.7 (2)
C8—C1—C2—C3175.33 (15)C5—C6—C14—C13109.25 (18)
C1—C2—C3—C40.9 (3)N1—C13—C14—C690.26 (18)
C1—C2—C3—O2177.59 (17)C10—C11—C16—O5176.56 (13)
C2—C3—C4—C50.1 (3)C12—C11—C16—O53.2 (2)
O2—C3—C4—C5177.16 (18)C10—C11—C16—C171.1 (2)
C2—C3—C4—O1177.33 (17)C12—C11—C16—C17178.70 (15)
O2—C3—C4—O10.1 (2)C11—C16—C17—O4177.48 (14)
C3—C4—C5—C60.6 (3)O5—C16—C17—O41.9 (2)
O1—C4—C5—C6177.3 (2)C11—C16—C17—C182.2 (2)
C2—C1—C6—C50.8 (3)O5—C16—C17—C18177.73 (14)
C8—C1—C6—C5175.64 (15)O4—C17—C18—C19177.98 (16)
C2—C1—C6—C14178.21 (16)C16—C17—C18—C191.7 (2)
C8—C1—C6—C145.3 (3)C17—C18—C19—C100.1 (3)
C4—C5—C6—C10.2 (3)C11—C10—C19—C181.0 (2)
C4—C5—C6—C14179.25 (17)C9—C10—C19—C18176.33 (15)
C2—C1—C8—O338.31 (19)C14—C13—N1—C1579.54 (18)
C6—C1—C8—O3145.11 (15)C14—C13—N1—C12150.04 (14)
C2—C1—C8—C979.68 (17)C11—C12—N1—C1580.48 (17)
C6—C1—C8—C996.90 (17)C11—C12—N1—C13148.58 (13)
O3—C8—C9—C1077.80 (16)C5—C4—O1—C7174.7 (2)
C1—C8—C9—C10161.39 (13)C3—C4—O1—C78.3 (2)
C8—C9—C10—C1989.37 (18)O2—C7—O1—C413.5 (2)
C8—C9—C10—C1193.35 (17)C2—C3—O2—C7174.7 (2)
C19—C10—C11—C160.5 (2)C4—C3—O2—C78.3 (2)
C9—C10—C11—C16176.82 (14)O1—C7—O2—C313.6 (2)
C19—C10—C11—C12179.70 (14)C18—C17—O4—C212.1 (3)
C9—C10—C11—C123.0 (2)C16—C17—O4—C21177.58 (18)
C16—C11—C12—N1121.81 (15)C11—C16—O5—C20112.30 (17)
C10—C11—C12—N158.39 (19)C17—C16—O5—C2072.12 (19)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
O3—H3···O5i0.822.032.8380 (16)168
C7—H7A···O4ii0.972.573.405 (3)144
C18—H18···O3iii0.932.533.229 (2)132
C7—H7B···Cg2iv0.972.573.464 (3)153
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x, y, z; (iv) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC21H25NO5
Mr371.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.2557 (19), 9.3705 (13), 15.278 (2)
β (°) 106.601 (2)
V3)1955.8 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.45 × 0.24 × 0.21
Data collection
DiffractometerBruker SMART APEX II CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.961, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
14189, 3646, 2766
Rint0.026
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.110, 1.02
No. of reflections3646
No. of parameters248
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
O3—H3···O5i0.822.032.8380 (16)168
C7—H7A···O4ii0.972.573.405 (3)144
C18—H18···O3iii0.932.533.229 (2)132
C7—H7B···Cg2iv0.972.573.464 (3)153
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1, y, z; (iii) x, y, z; (iv) x+1, y+1/2, z+1/2.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSF; No. 31172365; 31101469).

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCapasso, A., Piacente, S. & Pizza, C. (1997). Planta Med. 63, 326–328.  CrossRef CAS PubMed Web of Science
First citationJeong, E. J., Ma, C. J., Lee, K. Y., Kim, S. H., Sung, S. H. & Kim, Y. C. (2009). J. Ethnopharmacol. 121, 98–105.  Web of Science CrossRef PubMed
First citationMorteza, K., Amin, G., Shidfar, M. R., Hadizadeh, H. & Shafiee, A. (2003). Fitoterapia, 74, 493–496.  Web of Science PubMed
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationValpuesta, M., Diaz, A., Suau, R. & Torres, G. (2006). Eur. J. Org. Chem. pp. 964–971.  Web of Science CrossRef
First citationWada, Y., Kaga, H., Uchiito, S., Kumazawa, E., Tomiki, M., Onozaki, Y., Kurono, N., Tokuda, M., Ohkuma, T. & Orit, K. (2007). J. Org. Chem. 72, 7301–7306.  Web of Science CrossRef PubMed CAS
First citationYan, M., Sun, J. H., Lu, Z. Q., Chen, G. T., Guan, S. H., Liu, X., Jiang, B. H., Ye, M. & Guo, D. A. (2009). J. Chromatogr. A, 1216, 2045–2062.  Web of Science PubMed
First citationZhao, G., Jiang, Z. H., Zheng, X. W., Zang, S. Y. & Guo, L. H. (2008). Pharmacol. Biochem. Behav. 90, 363–371.  Web of Science CrossRef PubMed CAS

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds