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

Luo, G.; Chen, H.; Zhou, J.; Tian, D.-L.; Zhang, S.

doi:10.1107/S1600536811027735

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2087

doi:10.1107/S1600536811027735

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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

Gang Luo,^a Hong Chen,^b Jing Zhou,^a ^* Dan-Li Tian ^b,^c and Shi Zhang ^b,^c

^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 ); 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

Crystal data

C₂₇H₂₇NO₈
M_r = 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 ) T_min = 0.979, T_max = 0.987
14991 measured reflections
2950 independent reflections
2262 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯O7^iv	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); 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/S1600536811027735/rz2621sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027735/rz2621Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811027735/rz2621Isup3.cml

checkCIF report

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

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

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

C₂₇H₂₇NO₈	F(000) = 520
M_r = 493.50	D_x = 1.432 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4290 reflections
a = 11.7374 (15) Å	θ = 1.8–28.0°
b = 8.4087 (8) Å	µ = 0.11 mm⁻¹
c = 11.8848 (16) Å	T = 113 K
β = 102.693 (5)°	Prism, colourless
V = 1144.3 (2) Å³	0.20 × 0.18 × 0.12 mm
Z = 2

Data collection top

Rigaku Saturn724 CCD diffractometer	2950 independent reflections
Radiation source: rotating anode	2262 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.047
Detector resolution: 14.22 pixels mm^-1	θ_max = 28.0°, θ_min = 1.8°
ω and ϕ scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −11→10
T_min = 0.979, T_max = 0.987	l = −15→15
14991 measured 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.036P)²] where P = (F_o² + 2F_c²)/3
2950 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 0.17 e Å⁻³
41 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₇H₂₇NO₈	V = 1144.3 (2) Å³
M_r = 493.50	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.7374 (15) Å	µ = 0.11 mm⁻¹
b = 8.4087 (8) Å	T = 113 K
c = 11.8848 (16) Å	0.20 × 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)
T_min = 0.979, T_max = 0.987	R_int = 0.047
14991 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	41 restraints
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.17 e Å⁻³
2950 reflections	Δρ_min = −0.22 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	1.3701 (3)	0.9258 (3)	0.7345 (3)	0.0259 (8)	0.722 (7)
C1	1.4119 (3)	0.9416 (4)	0.6362 (3)	0.0258 (9)	0.722 (7)
H1A	1.4695	1.0165	0.6263	0.031*	0.722 (7)
C2	1.3609 (4)	0.8374 (6)	0.5562 (4)	0.0255 (13)	0.722 (7)
H2	1.3750	0.8249	0.4810	0.031*	0.722 (7)
C3	1.2805 (3)	0.7482 (5)	0.6062 (3)	0.0225 (8)	0.722 (7)
H3	1.2312	0.6647	0.5703	0.027*	0.722 (7)
C4	1.2879 (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'	1.3261	0.6824	0.4852	0.038*	0.278 (7)
C2'	1.3680 (11)	0.8821 (13)	0.5781 (10)	0.034 (5)	0.278 (7)
H2'	1.4078	0.9450	0.5325	0.040*	0.278 (7)
C3'	1.3437 (11)	0.9230 (11)	0.6900 (10)	0.027 (3)	0.278 (7)
H3'	1.3639	1.0178	0.7332	0.033*	0.278 (7)
C4'	1.2882 (10)	0.8003 (14)	0.7168 (9)	0.0219 (5)	0.278 (7)
O2	0.86595 (12)	0.7908 (2)	0.34547 (11)	0.0321 (4)
O3	0.67662 (11)	0.79787 (18)	0.36877 (11)	0.0236 (3)
O4	1.00549 (13)	0.9413 (2)	1.06166 (11)	0.0362 (4)
O5	0.81900 (13)	0.8872 (2)	1.05584 (13)	0.0388 (4)
O6	0.52676 (11)	1.28410 (17)	0.92051 (12)	0.0234 (3)
O7	0.62669 (11)	1.52498 (15)	0.83580 (11)	0.0185 (3)
O8	0.79077 (11)	1.47895 (16)	0.71823 (11)	0.0174 (3)
N1	1.10768 (16)	0.7428 (2)	0.77354 (18)	0.0272 (4)
C5	1.23354 (16)	0.7632 (3)	0.81295 (17)	0.0244 (5)
H5A	1.2492	0.8466	0.8694	0.029*	0.722 (7)
H5B	1.2673	0.6666	0.8485	0.029*	0.722 (7)
H5C	1.2489	0.8474	0.8688	0.029*	0.278 (7)
H5D	1.2669	0.6670	0.8495	0.029*	0.278 (7)
C6	1.04161 (16)	0.8907 (2)	0.75745 (16)	0.0186 (4)
H6	1.0923	0.9741	0.7336	0.022*
C7	0.93416 (15)	0.8704 (2)	0.65914 (16)	0.0164 (4)
C8	0.95707 (17)	0.8448 (3)	0.54918 (16)	0.0216 (4)
H8	1.0349	0.8434	0.5385	0.026*
C9	0.86540 (16)	0.8223 (2)	0.45889 (16)	0.0211 (4)
C10	0.74725 (18)	0.8030 (3)	0.28551 (17)	0.0291 (5)
H10A	0.7269	0.7138	0.2304	0.035*
H10B	0.7343	0.9040	0.2419	0.035*
C11	0.75225 (16)	0.8251 (2)	0.47291 (16)	0.0182 (4)
C12	0.72683 (16)	0.8476 (2)	0.57774 (16)	0.0168 (4)
H12	0.6483	0.8477	0.5863	0.020*
C13	0.81992 (16)	0.8708 (2)	0.67332 (16)	0.0159 (4)
C14	0.78895 (16)	0.8993 (2)	0.78943 (16)	0.0164 (4)
H14	0.7264	0.8221	0.7974	0.020*
C15	0.89755 (16)	0.8617 (2)	0.88232 (16)	0.0191 (4)
H15	0.9140	0.7457	0.8766	0.023*
C16	0.89706 (19)	0.8959 (3)	1.00600 (18)	0.0283 (5)
C17	1.08442 (18)	0.9333 (3)	0.98287 (17)	0.0280 (5)
H17A	1.1261	0.8302	0.9899	0.034*
H17B	1.1424	1.0205	0.9980	0.034*
C18	1.00434 (16)	0.9508 (3)	0.86503 (16)	0.0200 (4)
H18	0.9831	1.0657	0.8531	0.024*
C19	0.74248 (16)	1.0657 (2)	0.79825 (15)	0.0147 (4)
C20	0.78823 (15)	1.1934 (2)	0.74867 (16)	0.0151 (4)
H20	0.8466	1.1755	0.7060	0.018*
C21	0.74977 (15)	1.3459 (2)	0.76073 (15)	0.0148 (4)
C22	0.66214 (15)	1.3726 (2)	0.81994 (16)	0.0151 (4)
C23	0.61405 (15)	1.2451 (2)	0.86715 (16)	0.0166 (4)
C24	0.65474 (16)	1.0917 (2)	0.85763 (16)	0.0164 (4)
H24	0.6227	1.0050	0.8916	0.020*
C25	0.88269 (16)	1.4550 (2)	0.65900 (16)	0.0182 (4)
H25A	0.9504	1.4086	0.7120	0.027*
H25B	0.9048	1.5573	0.6304	0.027*
H25C	0.8561	1.3827	0.5938	0.027*
C26	0.54369 (17)	1.5820 (3)	0.73793 (18)	0.0254 (5)
H26A	0.5794	1.5843	0.6708	0.038*
H26B	0.5190	1.6896	0.7536	0.038*
H26C	0.4757	1.5113	0.7222	0.038*
C27	0.47759 (17)	1.1602 (3)	0.97667 (17)	0.0227 (5)
H27A	0.4453	1.0777	0.9204	0.034*
H27B	0.4153	1.2039	1.0104	0.034*
H27C	0.5384	1.1139	1.0378	0.034*
H1	1.086 (2)	0.676 (4)	0.803 (2)	0.056 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0233 (16)	0.0261 (14)	0.0294 (18)	0.0016 (11)	0.0081 (13)	−0.0019 (12)
C1	0.0237 (17)	0.0275 (18)	0.0266 (19)	0.0037 (14)	0.0063 (15)	0.0045 (16)
C2	0.021 (2)	0.031 (3)	0.023 (2)	0.003 (2)	0.0028 (15)	0.004 (2)
C3	0.0174 (17)	0.029 (2)	0.020 (2)	0.0030 (17)	0.0016 (14)	0.0017 (17)
C4	0.0147 (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)
O2	0.0278 (8)	0.0550 (11)	0.0151 (7)	−0.0014 (8)	0.0079 (6)	−0.0012 (7)
O3	0.0236 (7)	0.0315 (9)	0.0156 (7)	−0.0025 (7)	0.0038 (6)	−0.0010 (6)
O4	0.0300 (8)	0.0597 (12)	0.0172 (7)	0.0130 (8)	0.0012 (7)	−0.0025 (8)
O5	0.0378 (9)	0.0615 (12)	0.0202 (8)	0.0147 (8)	0.0132 (7)	0.0081 (8)
O6	0.0262 (7)	0.0208 (8)	0.0295 (8)	0.0029 (6)	0.0195 (6)	0.0037 (6)
O7	0.0215 (7)	0.0163 (7)	0.0186 (7)	0.0047 (6)	0.0065 (6)	0.0007 (6)
O8	0.0189 (7)	0.0149 (7)	0.0210 (7)	0.0012 (5)	0.0102 (6)	0.0022 (6)
N1	0.0166 (9)	0.0188 (10)	0.0440 (12)	0.0032 (8)	0.0019 (8)	0.0030 (9)
C5	0.0178 (10)	0.0288 (13)	0.0250 (11)	0.0052 (9)	0.0011 (8)	−0.0034 (9)
C6	0.0180 (9)	0.0163 (10)	0.0228 (10)	0.0021 (8)	0.0069 (8)	0.0021 (8)
C7	0.0190 (9)	0.0124 (9)	0.0187 (10)	0.0009 (8)	0.0062 (8)	0.0028 (8)
C8	0.0188 (9)	0.0261 (12)	0.0223 (10)	0.0008 (9)	0.0095 (8)	0.0043 (9)
C9	0.0269 (11)	0.0237 (11)	0.0154 (10)	0.0002 (9)	0.0107 (8)	0.0026 (9)
C10	0.0290 (11)	0.0415 (14)	0.0175 (10)	0.0022 (11)	0.0067 (9)	−0.0018 (10)
C11	0.0208 (10)	0.0160 (10)	0.0174 (9)	−0.0011 (8)	0.0031 (8)	0.0010 (8)
C12	0.0170 (9)	0.0144 (10)	0.0198 (10)	−0.0001 (8)	0.0062 (8)	0.0006 (8)
C13	0.0211 (9)	0.0107 (9)	0.0171 (9)	0.0019 (8)	0.0070 (8)	0.0019 (8)
C14	0.0181 (9)	0.0157 (10)	0.0170 (9)	0.0003 (8)	0.0070 (7)	0.0009 (8)
C15	0.0233 (10)	0.0188 (10)	0.0157 (9)	0.0058 (9)	0.0058 (8)	0.0035 (8)
C16	0.0304 (11)	0.0353 (13)	0.0189 (10)	0.0121 (11)	0.0050 (9)	0.0056 (10)
C17	0.0235 (11)	0.0377 (13)	0.0217 (10)	0.0083 (10)	0.0027 (9)	−0.0007 (10)
C18	0.0201 (10)	0.0217 (11)	0.0173 (9)	0.0040 (9)	0.0016 (8)	0.0019 (9)
C19	0.0152 (9)	0.0163 (10)	0.0122 (9)	0.0011 (8)	0.0020 (7)	−0.0005 (8)
C20	0.0132 (8)	0.0187 (10)	0.0139 (9)	0.0017 (8)	0.0042 (7)	0.0000 (7)
C21	0.0143 (8)	0.0178 (10)	0.0119 (9)	−0.0009 (8)	0.0017 (7)	0.0029 (8)
C22	0.0167 (9)	0.0144 (9)	0.0145 (9)	0.0035 (8)	0.0039 (7)	−0.0002 (8)
C23	0.0161 (9)	0.0207 (11)	0.0150 (9)	0.0015 (8)	0.0073 (7)	0.0005 (8)
C24	0.0179 (10)	0.0165 (10)	0.0155 (9)	−0.0018 (8)	0.0054 (8)	0.0016 (8)
C25	0.0186 (9)	0.0177 (10)	0.0212 (10)	−0.0037 (8)	0.0103 (8)	0.0001 (9)
C26	0.0224 (11)	0.0200 (11)	0.0323 (12)	0.0059 (9)	0.0030 (9)	0.0037 (9)
C27	0.0225 (11)	0.0262 (12)	0.0232 (11)	−0.0024 (9)	0.0129 (9)	0.0033 (9)

Geometric parameters (Å, º) top

O1—C1	1.370 (4)	C6—H6	1.0000
O1—C4	1.388 (5)	C7—C13	1.388 (2)
C1—C2	1.334 (5)	C7—C8	1.407 (2)
C1—H1A	0.9500	C8—C9	1.356 (3)
C2—C3	1.432 (6)	C8—H8	0.9500
C2—H2	0.9500	C9—C11	1.375 (2)
C3—C4	1.346 (5)	C10—H10A	0.9900
C3—H3	0.9500	C10—H10B	0.9900
C4—C5	1.502 (4)	C11—C12	1.357 (3)
O1'—C1'	1.360 (8)	C12—C13	1.406 (2)
O1'—C4'	1.374 (9)	C12—H12	0.9500
C1'—C2'	1.324 (9)	C13—C14	1.521 (2)
C1'—H1'	0.9500	C14—C19	1.514 (3)
C2'—C3'	1.461 (9)	C14—C15	1.525 (3)
C2'—H2'	0.9500	C14—H14	1.0000
C3'—C4'	1.297 (9)	C15—C16	1.499 (3)
C3'—H3'	0.9500	C15—C18	1.512 (3)
C4'—C5	1.461 (9)	C15—H15	1.0000
O2—C9	1.375 (2)	C17—C18	1.513 (3)
O2—C10	1.422 (2)	C17—H17A	0.9900
O3—C11	1.374 (2)	C17—H17B	0.9900
O3—C10	1.424 (2)	C18—H18	1.0000
O4—C16	1.354 (3)	C19—C24	1.388 (3)
O4—C17	1.456 (2)	C19—C20	1.389 (3)
O5—C16	1.198 (2)	C20—C21	1.377 (3)
O6—C23	1.358 (2)	C20—H20	0.9500
O6—C27	1.426 (2)	C21—C22	1.386 (2)
O7—C22	1.373 (2)	C22—C23	1.387 (3)
O7—C26	1.426 (2)	C23—C24	1.389 (3)
O8—C21	1.358 (2)	C24—H24	0.9500
O8—C25	1.426 (2)	C25—H25A	0.9800
N1—C6	1.456 (3)	C25—H25B	0.9800
N1—C5	1.458 (2)	C25—H25C	0.9800
N1—H1	0.74 (3)	C26—H26A	0.9800
C5—H5A	0.9601	C26—H26B	0.9800
C5—H5B	0.9600	C26—H26C	0.9800
C5—H5C	0.9600	C27—H27A	0.9800
C5—H5D	0.9600	C27—H27B	0.9800
C6—C18	1.525 (3)	C27—H27C	0.9800
C6—C7	1.529 (3)

C1—O1—C4	106.4 (3)	H10A—C10—H10B	108.5
C2—C1—O1	110.8 (3)	C12—C11—O3	128.41 (17)
C2—C1—H1A	124.6	C12—C11—C9	121.80 (18)
O1—C1—H1A	124.6	O3—C11—C9	109.76 (16)
C1—C2—C3	106.4 (4)	C11—C12—C13	118.20 (17)
C1—C2—H2	126.8	C11—C12—H12	120.9
C3—C2—H2	126.8	C13—C12—H12	120.9
C4—C3—C2	107.3 (3)	C7—C13—C12	120.12 (17)
C4—C3—H3	126.3	C7—C13—C14	122.71 (17)
C2—C3—H3	126.3	C12—C13—C14	117.16 (16)
C3—C4—O1	109.1 (3)	C19—C14—C13	111.73 (15)
C3—C4—C5	135.6 (4)	C19—C14—C15	113.45 (16)
O1—C4—C5	115.3 (4)	C13—C14—C15	107.20 (15)
C1'—O1'—C4'	102.4 (6)	C19—C14—H14	108.1
C2'—C1'—O1'	113.2 (8)	C13—C14—H14	108.1
C2'—C1'—H1'	123.4	C15—C14—H14	108.1
O1'—C1'—H1'	123.4	C16—C15—C18	102.73 (17)
C1'—C2'—C3'	105.3 (7)	C16—C15—C14	119.19 (16)
C1'—C2'—H2'	127.3	C18—C15—C14	112.65 (16)
C3'—C2'—H2'	127.3	C16—C15—H15	107.2
C4'—C3'—C2'	104.3 (7)	C18—C15—H15	107.2
C4'—C3'—H3'	127.9	C14—C15—H15	107.2
C2'—C3'—H3'	127.9	O5—C16—O4	120.97 (19)
C3'—C4'—O1'	114.9 (8)	O5—C16—C15	129.9 (2)
C3'—C4'—C5	133.9 (10)	O4—C16—C15	109.12 (17)
O1'—C4'—C5	111.2 (8)	O4—C17—C18	103.72 (15)
C9—O2—C10	105.20 (15)	O4—C17—H17A	111.0
C11—O3—C10	105.14 (14)	C18—C17—H17A	111.0
C16—O4—C17	109.59 (16)	O4—C17—H17B	111.0
C23—O6—C27	117.80 (15)	C18—C17—H17B	111.0
C22—O7—C26	112.03 (15)	H17A—C17—H17B	109.0
C21—O8—C25	115.83 (14)	C15—C18—C17	101.01 (16)
C6—N1—C5	114.47 (17)	C15—C18—C6	110.41 (17)
C6—N1—H1	119 (2)	C17—C18—C6	120.64 (16)
C5—N1—H1	112 (2)	C15—C18—H18	108.0
N1—C5—C4'	111.2 (5)	C17—C18—H18	108.0
N1—C5—C4	110.5 (2)	C6—C18—H18	108.0
N1—C5—H5A	109.6	C24—C19—C20	119.56 (17)
C4'—C5—H5A	109.9	C24—C19—C14	119.99 (16)
C4—C5—H5A	109.4	C20—C19—C14	120.45 (16)
N1—C5—H5B	109.4	C21—C20—C19	120.65 (17)
C4'—C5—H5B	108.4	C21—C20—H20	119.7
C4—C5—H5B	109.7	C19—C20—H20	119.7
H5A—C5—H5B	108.3	O8—C21—C20	125.24 (16)
N1—C5—H5C	109.4	O8—C21—C22	114.73 (17)
C4'—C5—H5C	109.6	C20—C21—C22	120.03 (17)
C4—C5—H5C	109.0	O7—C22—C21	120.13 (17)
H5B—C5—H5C	108.8	O7—C22—C23	120.24 (16)
N1—C5—H5D	109.3	C21—C22—C23	119.57 (17)
C4'—C5—H5D	109.2	O6—C23—C22	114.70 (17)
C4—C5—H5D	110.5	O6—C23—C24	124.80 (17)
H5A—C5—H5D	107.6	C22—C23—C24	120.50 (16)
H5C—C5—H5D	108.2	C19—C24—C23	119.65 (17)
N1—C6—C18	114.55 (17)	C19—C24—H24	120.2
N1—C6—C7	109.34 (16)	C23—C24—H24	120.2
C18—C6—C7	109.71 (14)	O8—C25—H25A	109.5
N1—C6—H6	107.7	O8—C25—H25B	109.5
C18—C6—H6	107.7	H25A—C25—H25B	109.5
C7—C6—H6	107.7	O8—C25—H25C	109.5
C13—C7—C8	120.00 (17)	H25A—C25—H25C	109.5
C13—C7—C6	124.32 (16)	H25B—C25—H25C	109.5
C8—C7—C6	115.65 (16)	O7—C26—H26A	109.5
C9—C8—C7	118.42 (17)	O7—C26—H26B	109.5
C9—C8—H8	120.8	H26A—C26—H26B	109.5
C7—C8—H8	120.8	O7—C26—H26C	109.5
C8—C9—C11	121.44 (18)	H26A—C26—H26C	109.5
C8—C9—O2	128.97 (17)	H26B—C26—H26C	109.5
C11—C9—O2	109.57 (17)	O6—C27—H27A	109.5
O2—C10—O3	107.78 (15)	O6—C27—H27B	109.5
O2—C10—H10A	110.2	H27A—C27—H27B	109.5
O3—C10—H10A	110.2	O6—C27—H27C	109.5
O2—C10—H10B	110.2	H27A—C27—H27C	109.5
O3—C10—H10B	110.2	H27B—C27—H27C	109.5

C4—O1—C1—C2	−0.1 (2)	C7—C13—C14—C19	103.5 (2)
O1—C1—C2—C3	0.0 (2)	C12—C13—C14—C19	−75.1 (2)
C1—C2—C3—C4	0.1 (3)	C7—C13—C14—C15	−21.3 (2)
C2—C3—C4—O1	−0.2 (4)	C12—C13—C14—C15	160.05 (17)
C2—C3—C4—C5	−177.2 (5)	C19—C14—C15—C16	49.7 (2)
C1—O1—C4—C3	0.2 (3)	C13—C14—C15—C16	173.51 (18)
C1—O1—C4—C5	177.9 (3)	C19—C14—C15—C18	−70.7 (2)
C4'—O1'—C1'—C2'	0.0 (3)	C13—C14—C15—C18	53.1 (2)
O1'—C1'—C2'—C3'	0.0 (3)	C17—O4—C16—O5	176.9 (2)
C1'—C2'—C3'—C4'	0.0 (5)	C17—O4—C16—C15	−2.7 (2)
C2'—C3'—C4'—O1'	0.0 (7)	C18—C15—C16—O5	160.0 (2)
C2'—C3'—C4'—C5	−176.7 (12)	C14—C15—C16—O5	34.7 (4)
C1'—O1'—C4'—C3'	0.0 (6)	C18—C15—C16—O4	−20.5 (2)
C1'—O1'—C4'—C5	177.4 (9)	C14—C15—C16—O4	−145.80 (18)
C6—N1—C5—C4'	−81.7 (5)	C16—O4—C17—C18	24.8 (2)
C6—N1—C5—C4	−80.5 (3)	C16—C15—C18—C17	33.8 (2)
C3'—C4'—C5—N1	115.8 (10)	C14—C15—C18—C17	163.25 (17)
O1'—C4'—C5—N1	−61.0 (8)	C16—C15—C18—C6	162.55 (16)
C3'—C4'—C5—C4	58 (30)	C14—C15—C18—C6	−68.0 (2)
O1'—C4'—C5—C4	−119 (30)	O4—C17—C18—C15	−35.8 (2)
C3—C4—C5—N1	−47.2 (6)	O4—C17—C18—C6	−157.70 (18)
O1—C4—C5—N1	136.0 (3)	N1—C6—C18—C15	−79.7 (2)
C3—C4—C5—C4'	75 (30)	C7—C6—C18—C15	43.7 (2)
O1—C4—C5—C4'	−102 (30)	N1—C6—C18—C17	37.5 (3)
C5—N1—C6—C18	−88.4 (2)	C7—C6—C18—C17	160.88 (19)
C5—N1—C6—C7	148.05 (17)	C13—C14—C19—C24	144.26 (17)
N1—C6—C7—C13	112.7 (2)	C15—C14—C19—C24	−94.4 (2)
C18—C6—C7—C13	−13.7 (3)	C13—C14—C19—C20	−36.7 (2)
N1—C6—C7—C8	−65.2 (2)	C15—C14—C19—C20	84.6 (2)
C18—C6—C7—C8	168.40 (17)	C24—C19—C20—C21	1.9 (3)
C13—C7—C8—C9	0.5 (3)	C14—C19—C20—C21	−177.17 (18)
C6—C7—C8—C9	178.49 (19)	C25—O8—C21—C20	−1.4 (2)
C7—C8—C9—C11	0.5 (3)	C25—O8—C21—C22	178.75 (15)
C7—C8—C9—O2	−177.89 (19)	C19—C20—C21—O8	178.27 (17)
C10—O2—C9—C8	−171.2 (2)	C19—C20—C21—C22	−1.9 (3)
C10—O2—C9—C11	10.3 (2)	C26—O7—C22—C21	83.0 (2)
C9—O2—C10—O3	−15.8 (2)	C26—O7—C22—C23	−99.73 (19)
C11—O3—C10—O2	15.3 (2)	O8—C21—C22—O7	−2.6 (2)
C10—O3—C11—C12	172.9 (2)	C20—C21—C22—O7	177.56 (16)
C10—O3—C11—C9	−9.0 (2)	O8—C21—C22—C23	−179.89 (16)
C8—C9—C11—C12	−1.2 (3)	C20—C21—C22—C23	0.3 (3)
O2—C9—C11—C12	177.42 (18)	C27—O6—C23—C22	−176.57 (16)
C8—C9—C11—O3	−179.50 (19)	C27—O6—C23—C24	3.8 (3)
O2—C9—C11—O3	−0.9 (2)	O7—C22—C23—O6	4.4 (2)
O3—C11—C12—C13	178.88 (18)	C21—C22—C23—O6	−178.29 (16)
C9—C11—C12—C13	0.9 (3)	O7—C22—C23—C24	−175.91 (18)
C8—C7—C13—C12	−0.8 (3)	C21—C22—C23—C24	1.4 (3)
C6—C7—C13—C12	−178.56 (18)	C20—C19—C24—C23	−0.2 (3)
C8—C7—C13—C14	−179.37 (18)	C14—C19—C24—C23	178.83 (17)
C6—C7—C13—C14	2.9 (3)	O6—C23—C24—C19	178.24 (17)
C11—C12—C13—C7	0.1 (3)	C22—C23—C24—C19	−1.4 (3)
C11—C12—C13—C14	178.72 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···O7^iv	0.98	2.50	2.993 (2)	111

Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+1, y+1/2, −z+1; (iii) x−1, y, z; (iv) −x+1, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₇NO₈
M_r	493.50
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	113
a, b, c (Å)	11.7374 (15), 8.4087 (8), 11.8848 (16)
β (°)	102.693 (5)
V (Å³)	1144.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.979, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	14991, 2950, 2262
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.067, 0.97
No. of reflections	2950
No. of parameters	372
No. of restraints	41
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C25—H25A···O2ⁱ	0.98	2.60	3.268 (2)	125.8
C26—H26C···O3ⁱⁱ	0.98	2.60	3.544 (3)	163.1
C27—H27A···O1ⁱⁱⁱ	0.98	2.54	3.487 (4)	163.5
C27—H27B···O7^iv	0.98	2.50	2.993 (2)	111.0

Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+1, y+1/2, −z+1; (iii) x−1, y, z; (iv) −x+1, y−1/2, −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

Feng, M., Zhao, M., Zhang, J., Yang, Z. & Chen, H. (2008). Acta Cryst. E64, o2339. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. CAS Google Scholar
Rigaku. (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, Y. L., Tropsha, A., McPhail, A. T. & Lee, K. H. (1994). J. Med. Chem. 37, 1460–1464. CSD CrossRef CAS PubMed Web of Science Google Scholar
Zhao, M., Feng, M., Bai, S. F., Zhang, Y., Bi, W. C. & Chen, H. (2009). Chin. Chem. Lett. 20, 901–904. Web of Science CrossRef CAS Google Scholar
Zuo, 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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