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

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ISSN: 2056-9890

9-[(Furan-2-ylmeth­yl)amino]-5-(3,4,5-trimeth­­oxy­phen­yl)-5,5a,8a,9-tetra­hydro­furo[3′,4′:6,7]naphtho­[2,3-d][1,3]dioxol-6(8H)-one

aSchool of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China, bRoom of Pharmacognosy, Medical College of Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China, and cTianjin Key Laboratory for Biomarkers of Occupational, and Environmental Hazards, Tianjin 300162, People's Republic of China
*Correspondence e-mail: zhoujing@tijmu.edu.cn

(Received 30 June 2011; accepted 11 July 2011; online 23 July 2011)

In title compound, C27H27NO8, the dihydrofuran-2(3H)-one ring and the six-membered ring fused to it both display envelope conformations. The dihedral angle between the benzene ring of the benzo[d][1,3]dioxole group and the other benzene ring is 60.59 (2)°. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The furan ring is disordered over two sets of sites with occupancies of 0.722 (7) and 0.278 (7)

Related literature

For podophyllotoxin derivatives synthesized by our group, see: Lu et al. (2010[Lu, Y. L., Zuo, S., Shi, S. Y., Li, X. C., Zhang, Y., Lv, J. J. & Chen, H. (2010). Chin. J. Med. Chem. 20, 90-95.]); Yu et al. (2008[Yu, P. F., Chen, H., Wang, J., He, C.-X., Cao, B., Li, M., Yang, N., Lei, Z.-Y. & Cheng, M. S. (2008). Chem. Pharm. Bull. 56, 831-834.]); Zhao et al. (2009[Zhao, M., Feng, M., Bai, S. F., Zhang, Y., Bi, W. C. & Chen, H. (2009). Chin. Chem. Lett. 20, 901-904.]). For bond-length and angle data of related structures, see: Feng et al. (2008[Feng, M., Zhao, M., Zhang, J., Yang, Z. & Chen, H. (2008). Acta Cryst. E64, o2339.]); Zhang et al. (1994[Zhang, Y. L., Tropsha, A., McPhail, A. T. & Lee, K. H. (1994). J. Med. Chem. 37, 1460-1464.]); Zuo et al. (2009[Zuo, S., Chen, H., Lu, Y., Cao, B. & Liu, D. (2009). Acta Cryst. E65, o3257.]).

[Scheme 1]

Experimental

Crystal data
  • C27H27NO8

  • Mr = 493.50

  • Monoclinic, P 21

  • a = 11.7374 (15) Å

  • b = 8.4087 (8) Å

  • c = 11.8848 (16) Å

  • β = 102.693 (5)°

  • V = 1144.3 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.12 mm

Data collection
  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007[Rigaku. (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.979, Tmax = 0.987

  • 14991 measured reflections

  • 2950 independent reflections

  • 2262 reflections with I > 2σ(I)

  • Rint = 0.047

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.067

  • S = 0.97

  • 2950 reflections

  • 372 parameters

  • 41 restraints

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

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C25—H25A⋯O2i 0.98 2.60 3.268 (2) 126
C26—H26C⋯O3ii 0.98 2.60 3.544 (3) 163
C27—H27A⋯O1iii 0.98 2.54 3.487 (4) 164
C27—H27B⋯O7iv 0.98 2.50 2.993 (2) 111
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+1]; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) x-1, y, z; (iv) [-x+1, y-{\script{1\over 2}}, -z+2].

Data collection: CrystalClear (Rigaku, 2007[Rigaku. (2007). 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

Podophyllotoxin and its derivatives are well known substances with anti-cancer activity. In recent years, our study has been aimed at synthesizing novel podophyllotoxin compounds with improved bioactivities (Lu et al., 2010; Yu et al., 2008; Zhao et al., 2009). In this paper, we report the crystal structure of title the compound.

In title compound, bond lengths and angles are normal and in good agreement with those reported previously for related compounds (Feng et al., 2008; Zhang, et al., 1994; Zuo, et al., 2009). The tetrahydrofuran ring (C15—C18/O4) and the six-membered ring (C6—C7/C13—C15/C18) fused to it both display envelope conformations. The dihedral angle between the benzene ring (C7—C9/C11—C13) of the benzo[d]-[1,3]dioxole fragment and the other benzene ring (C19—C24) is 60.59 (2)°. In the crystal structure, there are weak C—H···O intermolecular hydrogen interactions linking the molecules into a three-dimensional network (Table 1). The furan ring is disordered over two sets of sites with occupancies of 0.722 (7) and 0.278 (7).

Related literature top

For podophyllotoxin derivatives synthesized by our group, see: Lu et al. (2010); Yu et al. (2008); Zhao et al. (2009). For bond-length and angle data of related structures, see: Feng et al. (2008); Zhang et al. (1994); Zuo et al. (2009).

Experimental top

The title compound was synthesized by two steps. A mixture of furan-2-carbaldehyde (0.115 g, 1.2 mmol), 4β-amino podophyllotoxin (0.420 g, 1 mmol) and two drops of acetic acid in 95% ethanol (30 ml) was stirred for 6 h, then an appropriate amount of NaBH4was added and the mixture stirred for 1 h at 273 K. After the addition of 5% HCl (5 ml) to end off the reaction, the mixture was concentrated in vacuo and the pH adjusted to basic conditions with a saturated NaHCO3 solution. The reaction mixture was extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in methanol and slow evaporation over two weeks at room temperature gave colourless crystals suitable for X-ray analysis

Refinement top

All H atoms bound to C atoms were found in a difference Fourier map, and included in the final cycles of refinement using a riding model, with C—H = 0.95–1.00 Å and with Uiso(H) = 1.2Ueq(C) for aryl and methylene H atoms and 1.5Ueq(C) for the methyl H atoms. The amine H atom was refined freely. 690 Friedel pairs were merged. Similarity restraints in distances and thermal parameters were used in order to attain a reasonable geometry of the disordered furan ring.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); 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, with displacement ellipsoids drawn at the 40% probability level.
9-[(Furan-2-ylmethyl)amino]-5-(3,4,5-trimethoxyphenyl)- 5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol- 6(8H)-one top
Crystal data top
C27H27NO8F(000) = 520
Mr = 493.50Dx = 1.432 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4290 reflections
a = 11.7374 (15) Åθ = 1.8–28.0°
b = 8.4087 (8) ŵ = 0.11 mm1
c = 11.8848 (16) ÅT = 113 K
β = 102.693 (5)°Prism, colourless
V = 1144.3 (2) Å30.20 × 0.18 × 0.12 mm
Z = 2
Data collection top
Rigaku Saturn724 CCD
diffractometer
2950 independent reflections
Radiation source: rotating anode2262 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.047
Detector resolution: 14.22 pixels mm-1θmax = 28.0°, θmin = 1.8°
ω and ϕ scansh = 1515
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
k = 1110
Tmin = 0.979, Tmax = 0.987l = 1515
14991 measured 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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 0.97 w = 1/[σ2(Fo2) + (0.036P)2]
where P = (Fo2 + 2Fc2)/3
2950 reflections(Δ/σ)max = 0.001
372 parametersΔρmax = 0.17 e Å3
41 restraintsΔρmin = 0.22 e Å3
Crystal data top
C27H27NO8V = 1144.3 (2) Å3
Mr = 493.50Z = 2
Monoclinic, P21Mo Kα radiation
a = 11.7374 (15) ŵ = 0.11 mm1
b = 8.4087 (8) ÅT = 113 K
c = 11.8848 (16) Å0.20 × 0.18 × 0.12 mm
β = 102.693 (5)°
Data collection top
Rigaku Saturn724 CCD
diffractometer
2950 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
2262 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.987Rint = 0.047
14991 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03041 restraints
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.17 e Å3
2950 reflectionsΔρmin = 0.22 e Å3
372 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*/UeqOcc. (<1)
O11.3701 (3)0.9258 (3)0.7345 (3)0.0259 (8)0.722 (7)
C11.4119 (3)0.9416 (4)0.6362 (3)0.0258 (9)0.722 (7)
H1A1.46951.01650.62630.031*0.722 (7)
C21.3609 (4)0.8374 (6)0.5562 (4)0.0255 (13)0.722 (7)
H21.37500.82490.48100.031*0.722 (7)
C31.2805 (3)0.7482 (5)0.6062 (3)0.0225 (8)0.722 (7)
H31.23120.66470.57030.027*0.722 (7)
C41.2879 (4)0.8046 (6)0.7136 (4)0.0219 (5)0.722 (7)
O1'1.2713 (6)0.6797 (10)0.6369 (6)0.029 (2)0.278 (7)
C1'1.3229 (8)0.7386 (14)0.5538 (7)0.032 (3)0.278 (7)
H1'1.32610.68240.48520.038*0.278 (7)
C2'1.3680 (11)0.8821 (13)0.5781 (10)0.034 (5)0.278 (7)
H2'1.40780.94500.53250.040*0.278 (7)
C3'1.3437 (11)0.9230 (11)0.6900 (10)0.027 (3)0.278 (7)
H3'1.36391.01780.73320.033*0.278 (7)
C4'1.2882 (10)0.8003 (14)0.7168 (9)0.0219 (5)0.278 (7)
O20.86595 (12)0.7908 (2)0.34547 (11)0.0321 (4)
O30.67662 (11)0.79787 (18)0.36877 (11)0.0236 (3)
O41.00549 (13)0.9413 (2)1.06166 (11)0.0362 (4)
O50.81900 (13)0.8872 (2)1.05584 (13)0.0388 (4)
O60.52676 (11)1.28410 (17)0.92051 (12)0.0234 (3)
O70.62669 (11)1.52498 (15)0.83580 (11)0.0185 (3)
O80.79077 (11)1.47895 (16)0.71823 (11)0.0174 (3)
N11.10768 (16)0.7428 (2)0.77354 (18)0.0272 (4)
C51.23354 (16)0.7632 (3)0.81295 (17)0.0244 (5)
H5A1.24920.84660.86940.029*0.722 (7)
H5B1.26730.66660.84850.029*0.722 (7)
H5C1.24890.84740.86880.029*0.278 (7)
H5D1.26690.66700.84950.029*0.278 (7)
C61.04161 (16)0.8907 (2)0.75745 (16)0.0186 (4)
H61.09230.97410.73360.022*
C70.93416 (15)0.8704 (2)0.65914 (16)0.0164 (4)
C80.95707 (17)0.8448 (3)0.54918 (16)0.0216 (4)
H81.03490.84340.53850.026*
C90.86540 (16)0.8223 (2)0.45889 (16)0.0211 (4)
C100.74725 (18)0.8030 (3)0.28551 (17)0.0291 (5)
H10A0.72690.71380.23040.035*
H10B0.73430.90400.24190.035*
C110.75225 (16)0.8251 (2)0.47291 (16)0.0182 (4)
C120.72683 (16)0.8476 (2)0.57774 (16)0.0168 (4)
H120.64830.84770.58630.020*
C130.81992 (16)0.8708 (2)0.67332 (16)0.0159 (4)
C140.78895 (16)0.8993 (2)0.78943 (16)0.0164 (4)
H140.72640.82210.79740.020*
C150.89755 (16)0.8617 (2)0.88232 (16)0.0191 (4)
H150.91400.74570.87660.023*
C160.89706 (19)0.8959 (3)1.00600 (18)0.0283 (5)
C171.08442 (18)0.9333 (3)0.98287 (17)0.0280 (5)
H17A1.12610.83020.98990.034*
H17B1.14241.02050.99800.034*
C181.00434 (16)0.9508 (3)0.86503 (16)0.0200 (4)
H180.98311.06570.85310.024*
C190.74248 (16)1.0657 (2)0.79825 (15)0.0147 (4)
C200.78823 (15)1.1934 (2)0.74867 (16)0.0151 (4)
H200.84661.17550.70600.018*
C210.74977 (15)1.3459 (2)0.76073 (15)0.0148 (4)
C220.66214 (15)1.3726 (2)0.81994 (16)0.0151 (4)
C230.61405 (15)1.2451 (2)0.86715 (16)0.0166 (4)
C240.65474 (16)1.0917 (2)0.85763 (16)0.0164 (4)
H240.62271.00500.89160.020*
C250.88269 (16)1.4550 (2)0.65900 (16)0.0182 (4)
H25A0.95041.40860.71200.027*
H25B0.90481.55730.63040.027*
H25C0.85611.38270.59380.027*
C260.54369 (17)1.5820 (3)0.73793 (18)0.0254 (5)
H26A0.57941.58430.67080.038*
H26B0.51901.68960.75360.038*
H26C0.47571.51130.72220.038*
C270.47759 (17)1.1602 (3)0.97667 (17)0.0227 (5)
H27A0.44531.07770.92040.034*
H27B0.41531.20391.01040.034*
H27C0.53841.11391.03780.034*
H11.086 (2)0.676 (4)0.803 (2)0.056 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0233 (16)0.0261 (14)0.0294 (18)0.0016 (11)0.0081 (13)0.0019 (12)
C10.0237 (17)0.0275 (18)0.0266 (19)0.0037 (14)0.0063 (15)0.0045 (16)
C20.021 (2)0.031 (3)0.023 (2)0.003 (2)0.0028 (15)0.004 (2)
C30.0174 (17)0.029 (2)0.020 (2)0.0030 (17)0.0016 (14)0.0017 (17)
C40.0147 (9)0.0226 (12)0.0261 (11)0.0049 (9)0.0004 (8)0.0031 (9)
O1'0.027 (3)0.037 (5)0.022 (4)0.004 (3)0.002 (3)0.005 (3)
C1'0.030 (5)0.040 (6)0.024 (4)0.010 (5)0.002 (4)0.009 (4)
C2'0.037 (7)0.044 (8)0.022 (6)0.004 (5)0.010 (5)0.008 (6)
C3'0.031 (5)0.019 (5)0.031 (6)0.009 (4)0.007 (5)0.003 (4)
C4'0.0147 (9)0.0226 (12)0.0261 (11)0.0049 (9)0.0004 (8)0.0031 (9)
O20.0278 (8)0.0550 (11)0.0151 (7)0.0014 (8)0.0079 (6)0.0012 (7)
O30.0236 (7)0.0315 (9)0.0156 (7)0.0025 (7)0.0038 (6)0.0010 (6)
O40.0300 (8)0.0597 (12)0.0172 (7)0.0130 (8)0.0012 (7)0.0025 (8)
O50.0378 (9)0.0615 (12)0.0202 (8)0.0147 (8)0.0132 (7)0.0081 (8)
O60.0262 (7)0.0208 (8)0.0295 (8)0.0029 (6)0.0195 (6)0.0037 (6)
O70.0215 (7)0.0163 (7)0.0186 (7)0.0047 (6)0.0065 (6)0.0007 (6)
O80.0189 (7)0.0149 (7)0.0210 (7)0.0012 (5)0.0102 (6)0.0022 (6)
N10.0166 (9)0.0188 (10)0.0440 (12)0.0032 (8)0.0019 (8)0.0030 (9)
C50.0178 (10)0.0288 (13)0.0250 (11)0.0052 (9)0.0011 (8)0.0034 (9)
C60.0180 (9)0.0163 (10)0.0228 (10)0.0021 (8)0.0069 (8)0.0021 (8)
C70.0190 (9)0.0124 (9)0.0187 (10)0.0009 (8)0.0062 (8)0.0028 (8)
C80.0188 (9)0.0261 (12)0.0223 (10)0.0008 (9)0.0095 (8)0.0043 (9)
C90.0269 (11)0.0237 (11)0.0154 (10)0.0002 (9)0.0107 (8)0.0026 (9)
C100.0290 (11)0.0415 (14)0.0175 (10)0.0022 (11)0.0067 (9)0.0018 (10)
C110.0208 (10)0.0160 (10)0.0174 (9)0.0011 (8)0.0031 (8)0.0010 (8)
C120.0170 (9)0.0144 (10)0.0198 (10)0.0001 (8)0.0062 (8)0.0006 (8)
C130.0211 (9)0.0107 (9)0.0171 (9)0.0019 (8)0.0070 (8)0.0019 (8)
C140.0181 (9)0.0157 (10)0.0170 (9)0.0003 (8)0.0070 (7)0.0009 (8)
C150.0233 (10)0.0188 (10)0.0157 (9)0.0058 (9)0.0058 (8)0.0035 (8)
C160.0304 (11)0.0353 (13)0.0189 (10)0.0121 (11)0.0050 (9)0.0056 (10)
C170.0235 (11)0.0377 (13)0.0217 (10)0.0083 (10)0.0027 (9)0.0007 (10)
C180.0201 (10)0.0217 (11)0.0173 (9)0.0040 (9)0.0016 (8)0.0019 (9)
C190.0152 (9)0.0163 (10)0.0122 (9)0.0011 (8)0.0020 (7)0.0005 (8)
C200.0132 (8)0.0187 (10)0.0139 (9)0.0017 (8)0.0042 (7)0.0000 (7)
C210.0143 (8)0.0178 (10)0.0119 (9)0.0009 (8)0.0017 (7)0.0029 (8)
C220.0167 (9)0.0144 (9)0.0145 (9)0.0035 (8)0.0039 (7)0.0002 (8)
C230.0161 (9)0.0207 (11)0.0150 (9)0.0015 (8)0.0073 (7)0.0005 (8)
C240.0179 (10)0.0165 (10)0.0155 (9)0.0018 (8)0.0054 (8)0.0016 (8)
C250.0186 (9)0.0177 (10)0.0212 (10)0.0037 (8)0.0103 (8)0.0001 (9)
C260.0224 (11)0.0200 (11)0.0323 (12)0.0059 (9)0.0030 (9)0.0037 (9)
C270.0225 (11)0.0262 (12)0.0232 (11)0.0024 (9)0.0129 (9)0.0033 (9)
Geometric parameters (Å, º) top
O1—C11.370 (4)C6—H61.0000
O1—C41.388 (5)C7—C131.388 (2)
C1—C21.334 (5)C7—C81.407 (2)
C1—H1A0.9500C8—C91.356 (3)
C2—C31.432 (6)C8—H80.9500
C2—H20.9500C9—C111.375 (2)
C3—C41.346 (5)C10—H10A0.9900
C3—H30.9500C10—H10B0.9900
C4—C51.502 (4)C11—C121.357 (3)
O1'—C1'1.360 (8)C12—C131.406 (2)
O1'—C4'1.374 (9)C12—H120.9500
C1'—C2'1.324 (9)C13—C141.521 (2)
C1'—H1'0.9500C14—C191.514 (3)
C2'—C3'1.461 (9)C14—C151.525 (3)
C2'—H2'0.9500C14—H141.0000
C3'—C4'1.297 (9)C15—C161.499 (3)
C3'—H3'0.9500C15—C181.512 (3)
C4'—C51.461 (9)C15—H151.0000
O2—C91.375 (2)C17—C181.513 (3)
O2—C101.422 (2)C17—H17A0.9900
O3—C111.374 (2)C17—H17B0.9900
O3—C101.424 (2)C18—H181.0000
O4—C161.354 (3)C19—C241.388 (3)
O4—C171.456 (2)C19—C201.389 (3)
O5—C161.198 (2)C20—C211.377 (3)
O6—C231.358 (2)C20—H200.9500
O6—C271.426 (2)C21—C221.386 (2)
O7—C221.373 (2)C22—C231.387 (3)
O7—C261.426 (2)C23—C241.389 (3)
O8—C211.358 (2)C24—H240.9500
O8—C251.426 (2)C25—H25A0.9800
N1—C61.456 (3)C25—H25B0.9800
N1—C51.458 (2)C25—H25C0.9800
N1—H10.74 (3)C26—H26A0.9800
C5—H5A0.9601C26—H26B0.9800
C5—H5B0.9600C26—H26C0.9800
C5—H5C0.9600C27—H27A0.9800
C5—H5D0.9600C27—H27B0.9800
C6—C181.525 (3)C27—H27C0.9800
C6—C71.529 (3)
C1—O1—C4106.4 (3)H10A—C10—H10B108.5
C2—C1—O1110.8 (3)C12—C11—O3128.41 (17)
C2—C1—H1A124.6C12—C11—C9121.80 (18)
O1—C1—H1A124.6O3—C11—C9109.76 (16)
C1—C2—C3106.4 (4)C11—C12—C13118.20 (17)
C1—C2—H2126.8C11—C12—H12120.9
C3—C2—H2126.8C13—C12—H12120.9
C4—C3—C2107.3 (3)C7—C13—C12120.12 (17)
C4—C3—H3126.3C7—C13—C14122.71 (17)
C2—C3—H3126.3C12—C13—C14117.16 (16)
C3—C4—O1109.1 (3)C19—C14—C13111.73 (15)
C3—C4—C5135.6 (4)C19—C14—C15113.45 (16)
O1—C4—C5115.3 (4)C13—C14—C15107.20 (15)
C1'—O1'—C4'102.4 (6)C19—C14—H14108.1
C2'—C1'—O1'113.2 (8)C13—C14—H14108.1
C2'—C1'—H1'123.4C15—C14—H14108.1
O1'—C1'—H1'123.4C16—C15—C18102.73 (17)
C1'—C2'—C3'105.3 (7)C16—C15—C14119.19 (16)
C1'—C2'—H2'127.3C18—C15—C14112.65 (16)
C3'—C2'—H2'127.3C16—C15—H15107.2
C4'—C3'—C2'104.3 (7)C18—C15—H15107.2
C4'—C3'—H3'127.9C14—C15—H15107.2
C2'—C3'—H3'127.9O5—C16—O4120.97 (19)
C3'—C4'—O1'114.9 (8)O5—C16—C15129.9 (2)
C3'—C4'—C5133.9 (10)O4—C16—C15109.12 (17)
O1'—C4'—C5111.2 (8)O4—C17—C18103.72 (15)
C9—O2—C10105.20 (15)O4—C17—H17A111.0
C11—O3—C10105.14 (14)C18—C17—H17A111.0
C16—O4—C17109.59 (16)O4—C17—H17B111.0
C23—O6—C27117.80 (15)C18—C17—H17B111.0
C22—O7—C26112.03 (15)H17A—C17—H17B109.0
C21—O8—C25115.83 (14)C15—C18—C17101.01 (16)
C6—N1—C5114.47 (17)C15—C18—C6110.41 (17)
C6—N1—H1119 (2)C17—C18—C6120.64 (16)
C5—N1—H1112 (2)C15—C18—H18108.0
N1—C5—C4'111.2 (5)C17—C18—H18108.0
N1—C5—C4110.5 (2)C6—C18—H18108.0
N1—C5—H5A109.6C24—C19—C20119.56 (17)
C4'—C5—H5A109.9C24—C19—C14119.99 (16)
C4—C5—H5A109.4C20—C19—C14120.45 (16)
N1—C5—H5B109.4C21—C20—C19120.65 (17)
C4'—C5—H5B108.4C21—C20—H20119.7
C4—C5—H5B109.7C19—C20—H20119.7
H5A—C5—H5B108.3O8—C21—C20125.24 (16)
N1—C5—H5C109.4O8—C21—C22114.73 (17)
C4'—C5—H5C109.6C20—C21—C22120.03 (17)
C4—C5—H5C109.0O7—C22—C21120.13 (17)
H5B—C5—H5C108.8O7—C22—C23120.24 (16)
N1—C5—H5D109.3C21—C22—C23119.57 (17)
C4'—C5—H5D109.2O6—C23—C22114.70 (17)
C4—C5—H5D110.5O6—C23—C24124.80 (17)
H5A—C5—H5D107.6C22—C23—C24120.50 (16)
H5C—C5—H5D108.2C19—C24—C23119.65 (17)
N1—C6—C18114.55 (17)C19—C24—H24120.2
N1—C6—C7109.34 (16)C23—C24—H24120.2
C18—C6—C7109.71 (14)O8—C25—H25A109.5
N1—C6—H6107.7O8—C25—H25B109.5
C18—C6—H6107.7H25A—C25—H25B109.5
C7—C6—H6107.7O8—C25—H25C109.5
C13—C7—C8120.00 (17)H25A—C25—H25C109.5
C13—C7—C6124.32 (16)H25B—C25—H25C109.5
C8—C7—C6115.65 (16)O7—C26—H26A109.5
C9—C8—C7118.42 (17)O7—C26—H26B109.5
C9—C8—H8120.8H26A—C26—H26B109.5
C7—C8—H8120.8O7—C26—H26C109.5
C8—C9—C11121.44 (18)H26A—C26—H26C109.5
C8—C9—O2128.97 (17)H26B—C26—H26C109.5
C11—C9—O2109.57 (17)O6—C27—H27A109.5
O2—C10—O3107.78 (15)O6—C27—H27B109.5
O2—C10—H10A110.2H27A—C27—H27B109.5
O3—C10—H10A110.2O6—C27—H27C109.5
O2—C10—H10B110.2H27A—C27—H27C109.5
O3—C10—H10B110.2H27B—C27—H27C109.5
C4—O1—C1—C20.1 (2)C7—C13—C14—C19103.5 (2)
O1—C1—C2—C30.0 (2)C12—C13—C14—C1975.1 (2)
C1—C2—C3—C40.1 (3)C7—C13—C14—C1521.3 (2)
C2—C3—C4—O10.2 (4)C12—C13—C14—C15160.05 (17)
C2—C3—C4—C5177.2 (5)C19—C14—C15—C1649.7 (2)
C1—O1—C4—C30.2 (3)C13—C14—C15—C16173.51 (18)
C1—O1—C4—C5177.9 (3)C19—C14—C15—C1870.7 (2)
C4'—O1'—C1'—C2'0.0 (3)C13—C14—C15—C1853.1 (2)
O1'—C1'—C2'—C3'0.0 (3)C17—O4—C16—O5176.9 (2)
C1'—C2'—C3'—C4'0.0 (5)C17—O4—C16—C152.7 (2)
C2'—C3'—C4'—O1'0.0 (7)C18—C15—C16—O5160.0 (2)
C2'—C3'—C4'—C5176.7 (12)C14—C15—C16—O534.7 (4)
C1'—O1'—C4'—C3'0.0 (6)C18—C15—C16—O420.5 (2)
C1'—O1'—C4'—C5177.4 (9)C14—C15—C16—O4145.80 (18)
C6—N1—C5—C4'81.7 (5)C16—O4—C17—C1824.8 (2)
C6—N1—C5—C480.5 (3)C16—C15—C18—C1733.8 (2)
C3'—C4'—C5—N1115.8 (10)C14—C15—C18—C17163.25 (17)
O1'—C4'—C5—N161.0 (8)C16—C15—C18—C6162.55 (16)
C3'—C4'—C5—C458 (30)C14—C15—C18—C668.0 (2)
O1'—C4'—C5—C4119 (30)O4—C17—C18—C1535.8 (2)
C3—C4—C5—N147.2 (6)O4—C17—C18—C6157.70 (18)
O1—C4—C5—N1136.0 (3)N1—C6—C18—C1579.7 (2)
C3—C4—C5—C4'75 (30)C7—C6—C18—C1543.7 (2)
O1—C4—C5—C4'102 (30)N1—C6—C18—C1737.5 (3)
C5—N1—C6—C1888.4 (2)C7—C6—C18—C17160.88 (19)
C5—N1—C6—C7148.05 (17)C13—C14—C19—C24144.26 (17)
N1—C6—C7—C13112.7 (2)C15—C14—C19—C2494.4 (2)
C18—C6—C7—C1313.7 (3)C13—C14—C19—C2036.7 (2)
N1—C6—C7—C865.2 (2)C15—C14—C19—C2084.6 (2)
C18—C6—C7—C8168.40 (17)C24—C19—C20—C211.9 (3)
C13—C7—C8—C90.5 (3)C14—C19—C20—C21177.17 (18)
C6—C7—C8—C9178.49 (19)C25—O8—C21—C201.4 (2)
C7—C8—C9—C110.5 (3)C25—O8—C21—C22178.75 (15)
C7—C8—C9—O2177.89 (19)C19—C20—C21—O8178.27 (17)
C10—O2—C9—C8171.2 (2)C19—C20—C21—C221.9 (3)
C10—O2—C9—C1110.3 (2)C26—O7—C22—C2183.0 (2)
C9—O2—C10—O315.8 (2)C26—O7—C22—C2399.73 (19)
C11—O3—C10—O215.3 (2)O8—C21—C22—O72.6 (2)
C10—O3—C11—C12172.9 (2)C20—C21—C22—O7177.56 (16)
C10—O3—C11—C99.0 (2)O8—C21—C22—C23179.89 (16)
C8—C9—C11—C121.2 (3)C20—C21—C22—C230.3 (3)
O2—C9—C11—C12177.42 (18)C27—O6—C23—C22176.57 (16)
C8—C9—C11—O3179.50 (19)C27—O6—C23—C243.8 (3)
O2—C9—C11—O30.9 (2)O7—C22—C23—O64.4 (2)
O3—C11—C12—C13178.88 (18)C21—C22—C23—O6178.29 (16)
C9—C11—C12—C130.9 (3)O7—C22—C23—C24175.91 (18)
C8—C7—C13—C120.8 (3)C21—C22—C23—C241.4 (3)
C6—C7—C13—C12178.56 (18)C20—C19—C24—C230.2 (3)
C8—C7—C13—C14179.37 (18)C14—C19—C24—C23178.83 (17)
C6—C7—C13—C142.9 (3)O6—C23—C24—C19178.24 (17)
C11—C12—C13—C70.1 (3)C22—C23—C24—C191.4 (3)
C11—C12—C13—C14178.72 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25A···O2i0.982.603.268 (2)126
C26—H26C···O3ii0.982.603.544 (3)163
C27—H27A···O1iii0.982.543.487 (4)164
C27—H27B···O7iv0.982.502.993 (2)111
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+1, y+1/2, z+1; (iii) x1, y, z; (iv) x+1, y1/2, z+2.

Experimental details

Crystal data
Chemical formulaC27H27NO8
Mr493.50
Crystal system, space groupMonoclinic, P21
Temperature (K)113
a, b, c (Å)11.7374 (15), 8.4087 (8), 11.8848 (16)
β (°) 102.693 (5)
V3)1144.3 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.20 × 0.18 × 0.12
Data collection
DiffractometerRigaku Saturn724 CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2007)
Tmin, Tmax0.979, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
14991, 2950, 2262
Rint0.047
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.067, 0.97
No. of reflections2950
No. of parameters372
No. of restraints41
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.22

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25A···O2i0.982.603.268 (2)125.8
C26—H26C···O3ii0.982.603.544 (3)163.1
C27—H27A···O1iii0.982.543.487 (4)163.5
C27—H27B···O7iv0.982.502.993 (2)111.0
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+1, y+1/2, z+1; (iii) x1, y, z; (iv) x+1, y1/2, z+2.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 30873363), the Program of the Science Foundation of Tianjin (08JCYBJC070000) and the Major Program of the Science Foundation of Tianjin (09ZCKFSH01700).

References

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First citationYu, P. F., Chen, H., Wang, J., He, C.-X., Cao, B., Li, M., Yang, N., Lei, Z.-Y. & Cheng, M. S. (2008). Chem. Pharm. Bull. 56, 831–834.  Web of Science CrossRef PubMed CAS Google Scholar
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First citationZuo, S., Chen, H., Lu, Y., Cao, B. & Liu, D. (2009). Acta Cryst. E65, o3257.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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