9-[(2-Chloro­benz­yl)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

Zhu, T.-L.; Jin, J.-R.; Chen, H.; Chen, L.-T.; Liu, J.

doi:10.1107/S1600536811018289

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1491

doi:10.1107/S1600536811018289

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9-[(2-Chlorobenzyl)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

Tie-Liang Zhu,^a Jie-Ru Jin,^b Hong Chen,^c,^d Li-Ting Chen ^d and Jing Liu ^d ^*

^aThe Affiliated Hospital of the Medical College of the Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China, ^bThe General Unit of the Chinese People's Armed Police Force Hospital in Tianjin, Tianjin 300252, People's Republic of China, ^cTianjin Key Laboratory for Biomarkers of Occupational and Environmental Hazards, Tianjin 300162, People's Republic of China, and ^dRoom of Pharmacognosy, Medical College of the Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China
^*Correspondence e-mail: liujing870421@yahoo.cn

(Received 8 May 2011; accepted 13 May 2011; online 25 May 2011)

In the title compound, C₂₉H₂₈ClNO₇, the tetrahydrofuran ring and the six-membered ring fused to it both display envelope conformations. The dihedral angles between the plane of the benzene ring of the benzo[d][1,3]dioxole system and the planes of the other two benzene rings are 80.59 (3) and 63.60 (2)°.

Related literature

For bond-length and angle data for similar structures, see: Feng et al. (2008 ); Zhang et al. (1994 ); Zuo et al. (2009 ).

Experimental

Crystal data

C₂₉H₂₈ClNO₇
M_r = 537.97
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.0971 (14) Å
b = 15.264 (2) Å
c = 16.220 (2) Å
V = 2499.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.960, T_max = 0.976
26247 measured reflections
5968 independent reflections
5580 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.066
S = 1.03
5968 reflections
350 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983), 2615 Friedel pairs
Flack parameter: 0.00 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O7ⁱ	0.95	2.56	3.2130 (18)	126
Symmetry code: (i) x, y-1, z.

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018289/hg5035sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018289/hg5035Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018289/hg5035Isup3.cml

checkCIF report

Comment top

Podophyllotoxin and their derivatives are well known as substances with anti-cancer activity. In recent years, our study are paying attention to synthesize different kinds of Podophyllotoxin compounds and aim at the discovery of new derivatives with improved bioactivities. In this paper, we reported the crystal structure of title compound.

In title compound, C₂₉H₂₈ClNO₇, bond lengths and angles are normal and in good agreement with those reported previously (Feng et al., 2008; Zhang, et al., 1994; Zuo, et al., 2009). The tetrahydrofuran ring (C1/C2/C12/C30/O3) and the six-membered ring (C2—C4/C10—C12)fused to it both display envelope conformations. The dihedral angles between the benzene ring (C4—C10) of the benzo[d]-[1,3]dioxole and the other two benzene ring (C13—C18 and C23—C28) are 80.59 (3) and 63.60 (2)°, respectively. There are weaker C—H···O intermolecular interactions, which stabilized the structure (Table 1).

Related literature top

For bond-length and angle data for similar structures, see: Feng et al. (2008); Zhang et al. (1994); Zuo et al. (2009).

Experimental top

The target compound was synthesized by two steps. 2-chlorobenzaldehyde, 4β-amino podophyllotoxin, two drops of acetic acid in 95% ethanol was stirred for 6 h. Appropriate amount of NaBH₄ was added into the reaction mixture to stirred for 1 h at 273 K. Then add 5% HCl to end off the reaction, the reaction mixture was concentrated in vacuo. Add saturated NaHCO₃ to adjust PH>7. The reaction mixture was extracted with CH₂Cl₂ and dried over MgSO₄ and concentrated in vacuo. The residue was resolved in a methanol solution and slow evaporation over two weeks at room temperature gave transparent 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 40% probability level.

9-[(2-Chlorobenzyl)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

C₂₉H₂₈ClNO₇	F(000) = 1128
M_r = 537.97	D_x = 1.429 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8535 reflections
a = 10.0971 (14) Å	θ = 1.3–27.9°
b = 15.264 (2) Å	µ = 0.20 mm⁻¹
c = 16.220 (2) Å	T = 113 K
V = 2499.9 (6) Å³	Prism, colorless
Z = 4	0.20 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5968 independent reflections
Radiation source: rotating anode	5580 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.044
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 1.8°
ω and ϕ scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −20→20
T_min = 0.960, T_max = 0.976	l = −20→21
26247 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0324P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5968 reflections	Δρ_max = 0.18 e Å⁻³
350 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2615 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (4)

Crystal data top

C₂₉H₂₈ClNO₇	V = 2499.9 (6) Å³
M_r = 537.97	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.0971 (14) Å	µ = 0.20 mm⁻¹
b = 15.264 (2) Å	T = 113 K
c = 16.220 (2) Å	0.20 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5968 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	5580 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.976	R_int = 0.044
26247 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	Δρ_max = 0.18 e Å⁻³
S = 1.03	Δρ_min = −0.25 e Å⁻³
5968 reflections	Absolute structure: Flack (1983), 2615 Friedel pairs
350 parameters	Absolute structure parameter: 0.00 (4)
0 restraints

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
Cl1	−0.19083 (4)	−0.19218 (2)	0.81504 (2)	0.02120 (9)
O1	0.56079 (11)	0.23021 (7)	0.72078 (6)	0.0247 (3)
O2	0.41961 (12)	0.14072 (7)	0.64668 (6)	0.0240 (3)
O3	0.09055 (11)	0.06096 (7)	1.11792 (6)	0.0253 (3)
O4	0.28209 (11)	0.10425 (6)	1.17321 (6)	0.0261 (3)
O5	0.31178 (11)	0.40151 (6)	1.20050 (6)	0.0209 (2)
O6	0.18781 (11)	0.51133 (6)	1.09222 (6)	0.0189 (2)
O7	0.12116 (11)	0.45705 (6)	0.94280 (6)	0.0209 (2)
N1	0.16797 (13)	−0.03792 (7)	0.88773 (8)	0.0199 (3)
C1	0.03959 (16)	0.03821 (10)	1.03598 (9)	0.0229 (3)
H1A	−0.0550	0.0545	1.0307	0.027*
H1B	0.0491	−0.0253	1.0253	0.027*
C2	0.12467 (15)	0.09136 (9)	0.97679 (9)	0.0178 (3)
H2	0.0883	0.1522	0.9740	0.021*
C3	0.14712 (15)	0.05866 (8)	0.88890 (9)	0.0180 (3)
H3	0.0667	0.0725	0.8554	0.022*
C4	0.26551 (15)	0.10614 (8)	0.85124 (9)	0.0162 (3)
C5	0.28349 (15)	0.09545 (9)	0.76558 (9)	0.0193 (3)
H5	0.2256	0.0594	0.7343	0.023*
C6	0.38597 (16)	0.13821 (9)	0.72912 (9)	0.0189 (3)
C7	0.54559 (17)	0.18360 (12)	0.64454 (10)	0.0287 (4)
H7A	0.5496	0.2248	0.5975	0.034*
H7B	0.6174	0.1399	0.6382	0.034*
C8	0.47041 (15)	0.19194 (10)	0.77350 (9)	0.0185 (3)
C9	0.45689 (15)	0.20311 (9)	0.85659 (9)	0.0180 (3)
H9	0.5156	0.2400	0.8865	0.022*
C10	0.35316 (15)	0.15831 (8)	0.89679 (9)	0.0163 (3)
C11	0.34335 (15)	0.16871 (8)	0.99015 (8)	0.0161 (3)
H11	0.4342	0.1599	1.0133	0.019*
C12	0.25620 (15)	0.09411 (9)	1.02231 (9)	0.0179 (3)
H12	0.3033	0.0382	1.0093	0.021*
C13	0.29684 (15)	0.25985 (8)	1.01666 (8)	0.0158 (3)
C14	0.32622 (15)	0.28769 (8)	1.09600 (9)	0.0168 (3)
H14	0.3742	0.2503	1.1320	0.020*
C15	0.28577 (15)	0.37031 (9)	1.12340 (8)	0.0158 (3)
C16	0.21789 (15)	0.42648 (8)	1.07030 (8)	0.0158 (3)
C17	0.18852 (15)	0.39801 (8)	0.99061 (8)	0.0157 (3)
C18	0.22750 (14)	0.31519 (9)	0.96379 (9)	0.0165 (3)
H18	0.2068	0.2965	0.9094	0.020*
C19	0.37066 (17)	0.34058 (10)	1.25669 (9)	0.0248 (4)
H19A	0.3180	0.2867	1.2580	0.037*
H19B	0.3734	0.3664	1.3120	0.037*
H19C	0.4609	0.3270	1.2386	0.037*
C20	0.08614 (17)	0.52134 (10)	1.15354 (10)	0.0233 (4)
H20A	0.0070	0.4889	1.1365	0.035*
H20B	0.0642	0.5836	1.1596	0.035*
H20C	0.1179	0.4984	1.2064	0.035*
C21	0.10712 (18)	0.43615 (10)	0.85726 (9)	0.0254 (4)
H21A	0.1949	0.4285	0.8325	0.038*
H21B	0.0604	0.4838	0.8291	0.038*
H21C	0.0564	0.3818	0.8515	0.038*
C22	0.04768 (15)	−0.08553 (9)	0.86421 (9)	0.0193 (3)
H22A	0.0434	−0.0891	0.8033	0.023*
H22B	−0.0305	−0.0519	0.8832	0.023*
C23	0.04024 (15)	−0.17743 (9)	0.89942 (8)	0.0157 (3)
C24	0.13828 (16)	−0.21272 (9)	0.94947 (9)	0.0196 (3)
H24	0.2148	−0.1789	0.9617	0.024*
C25	0.12665 (16)	−0.29669 (9)	0.98209 (9)	0.0218 (3)
H25	0.1958	−0.3201	1.0151	0.026*
C26	0.01461 (16)	−0.34623 (10)	0.96657 (9)	0.0206 (3)
H26	0.0055	−0.4028	0.9904	0.025*
C27	−0.08436 (15)	−0.31306 (9)	0.91619 (8)	0.0184 (3)
H27	−0.1614	−0.3467	0.9049	0.022*
C28	−0.06935 (15)	−0.23039 (9)	0.88264 (8)	0.0165 (3)
C30	0.21676 (16)	0.08957 (9)	1.11209 (9)	0.0211 (3)
H1	0.2339 (18)	−0.0558 (10)	0.8486 (10)	0.029 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01945 (19)	0.02013 (16)	0.02402 (18)	−0.00103 (16)	−0.00483 (16)	0.00179 (14)
O1	0.0245 (6)	0.0268 (6)	0.0227 (6)	−0.0046 (5)	0.0060 (5)	−0.0004 (4)
O2	0.0276 (7)	0.0272 (6)	0.0172 (5)	−0.0013 (5)	0.0006 (5)	−0.0011 (4)
O3	0.0264 (7)	0.0266 (6)	0.0229 (6)	−0.0033 (5)	0.0008 (5)	0.0018 (5)
O4	0.0340 (7)	0.0244 (5)	0.0200 (6)	−0.0020 (5)	−0.0058 (5)	0.0028 (4)
O5	0.0264 (6)	0.0203 (5)	0.0160 (5)	−0.0005 (5)	−0.0052 (5)	−0.0020 (4)
O6	0.0253 (6)	0.0112 (4)	0.0203 (5)	−0.0021 (5)	0.0045 (5)	−0.0013 (4)
O7	0.0305 (6)	0.0163 (5)	0.0159 (5)	0.0054 (5)	−0.0063 (5)	0.0013 (4)
N1	0.0177 (7)	0.0138 (6)	0.0282 (7)	0.0003 (5)	−0.0035 (6)	−0.0016 (5)
C1	0.0202 (9)	0.0249 (8)	0.0234 (8)	−0.0020 (7)	−0.0009 (7)	0.0017 (6)
C2	0.0168 (8)	0.0154 (7)	0.0213 (7)	0.0017 (6)	−0.0017 (6)	0.0016 (6)
C3	0.0163 (8)	0.0147 (7)	0.0230 (8)	0.0008 (6)	−0.0051 (6)	−0.0003 (6)
C4	0.0178 (8)	0.0104 (6)	0.0203 (7)	0.0030 (6)	−0.0027 (6)	0.0012 (5)
C5	0.0213 (8)	0.0140 (6)	0.0227 (8)	0.0009 (6)	−0.0054 (6)	−0.0020 (6)
C6	0.0232 (9)	0.0165 (7)	0.0171 (8)	0.0050 (6)	−0.0008 (6)	0.0017 (6)
C7	0.0255 (9)	0.0387 (10)	0.0219 (8)	−0.0006 (8)	0.0017 (7)	0.0007 (7)
C8	0.0170 (8)	0.0152 (7)	0.0232 (8)	0.0026 (7)	0.0003 (6)	0.0023 (6)
C9	0.0176 (8)	0.0142 (7)	0.0221 (8)	0.0001 (6)	−0.0023 (6)	−0.0031 (6)
C10	0.0179 (8)	0.0126 (6)	0.0182 (7)	0.0059 (6)	−0.0010 (6)	−0.0014 (5)
C11	0.0169 (8)	0.0164 (7)	0.0151 (7)	0.0013 (6)	−0.0033 (6)	0.0010 (5)
C12	0.0184 (8)	0.0139 (6)	0.0214 (8)	0.0027 (6)	−0.0028 (6)	0.0012 (6)
C13	0.0142 (8)	0.0153 (7)	0.0179 (7)	−0.0017 (6)	0.0000 (7)	0.0002 (5)
C14	0.0157 (8)	0.0161 (7)	0.0187 (7)	0.0005 (6)	−0.0041 (6)	0.0036 (5)
C15	0.0154 (8)	0.0179 (6)	0.0140 (7)	−0.0047 (6)	−0.0006 (6)	−0.0013 (5)
C16	0.0181 (8)	0.0125 (6)	0.0169 (7)	−0.0027 (6)	0.0024 (6)	−0.0017 (5)
C17	0.0148 (7)	0.0146 (6)	0.0178 (7)	−0.0023 (6)	0.0002 (6)	0.0030 (5)
C18	0.0174 (7)	0.0169 (7)	0.0152 (7)	−0.0020 (6)	0.0010 (6)	−0.0006 (6)
C19	0.0292 (9)	0.0276 (8)	0.0175 (8)	−0.0019 (7)	−0.0070 (7)	0.0028 (6)
C20	0.0239 (9)	0.0189 (8)	0.0272 (9)	−0.0012 (6)	0.0056 (7)	−0.0033 (6)
C21	0.0386 (10)	0.0215 (8)	0.0160 (8)	−0.0003 (7)	−0.0056 (7)	0.0025 (6)
C22	0.0196 (8)	0.0172 (7)	0.0213 (8)	−0.0031 (6)	−0.0033 (6)	0.0018 (6)
C23	0.0182 (8)	0.0151 (7)	0.0138 (7)	0.0006 (6)	0.0017 (6)	−0.0017 (5)
C24	0.0202 (8)	0.0212 (8)	0.0174 (7)	−0.0011 (6)	−0.0004 (6)	−0.0022 (6)
C25	0.0274 (9)	0.0211 (8)	0.0169 (7)	0.0059 (7)	−0.0040 (7)	0.0001 (6)
C26	0.0284 (9)	0.0158 (7)	0.0174 (7)	0.0022 (6)	0.0046 (7)	0.0003 (6)
C27	0.0200 (8)	0.0183 (7)	0.0169 (7)	−0.0029 (7)	0.0044 (6)	−0.0025 (6)
C28	0.0168 (8)	0.0189 (7)	0.0139 (7)	0.0018 (6)	0.0002 (6)	−0.0018 (6)
C30	0.0246 (9)	0.0143 (7)	0.0245 (8)	0.0018 (6)	−0.0008 (7)	0.0032 (6)

Geometric parameters (Å, º) top

Cl1—C28	1.7455 (15)	C11—C13	1.5301 (19)
O1—C8	1.3803 (18)	C11—C12	1.531 (2)
O1—C7	1.4348 (18)	C11—H11	1.0000
O2—C6	1.3802 (17)	C12—C30	1.511 (2)
O2—C7	1.431 (2)	C12—H12	1.0000
O3—C30	1.3504 (19)	C13—C14	1.3874 (19)
O3—C1	1.4669 (18)	C13—C18	1.3925 (19)
O4—C30	1.2116 (18)	C14—C15	1.3981 (19)
O5—C15	1.3637 (16)	C14—H14	0.9500
O5—C19	1.4315 (17)	C15—C16	1.395 (2)
O6—C16	1.3771 (16)	C16—C17	1.3956 (19)
O6—C20	1.4374 (18)	C17—C18	1.3937 (19)
O7—C17	1.3697 (17)	C18—H18	0.9500
O7—C21	1.4307 (18)	C19—H19A	0.9800
N1—C22	1.4659 (19)	C19—H19B	0.9800
N1—C3	1.4892 (17)	C19—H19C	0.9800
N1—H1	0.959 (17)	C20—H20A	0.9800
C1—C2	1.522 (2)	C20—H20B	0.9800
C1—H1A	0.9900	C20—H20C	0.9800
C1—H1B	0.9900	C21—H21A	0.9800
C2—C12	1.520 (2)	C21—H21B	0.9800
C2—C3	1.527 (2)	C21—H21C	0.9800
C2—H2	1.0000	C22—C23	1.5164 (19)
C3—C4	1.526 (2)	C22—H22A	0.9900
C3—H3	1.0000	C22—H22B	0.9900
C4—C10	1.401 (2)	C23—C24	1.389 (2)
C4—C5	1.411 (2)	C23—C28	1.397 (2)
C5—C6	1.359 (2)	C24—C25	1.392 (2)
C5—H5	0.9500	C24—H24	0.9500
C6—C8	1.385 (2)	C25—C26	1.384 (2)
C7—H7A	0.9900	C25—H25	0.9500
C7—H7B	0.9900	C26—C27	1.387 (2)
C8—C9	1.3654 (19)	C26—H26	0.9500
C9—C10	1.411 (2)	C27—C28	1.383 (2)
C9—H9	0.9500	C27—H27	0.9500
C10—C11	1.526 (2)

C8—O1—C7	104.68 (11)	C14—C13—C18	119.54 (12)
C6—O2—C7	104.77 (12)	C14—C13—C11	118.26 (12)
C30—O3—C1	110.13 (12)	C18—C13—C11	122.19 (12)
C15—O5—C19	115.91 (11)	C13—C14—C15	120.58 (13)
C16—O6—C20	115.86 (10)	C13—C14—H14	119.7
C17—O7—C21	116.85 (11)	C15—C14—H14	119.7
C22—N1—C3	112.14 (11)	O5—C15—C16	116.50 (12)
C22—N1—H1	105.2 (10)	O5—C15—C14	123.39 (12)
C3—N1—H1	112.8 (10)	C16—C15—C14	120.10 (13)
O3—C1—C2	104.31 (12)	O6—C16—C15	121.80 (12)
O3—C1—H1A	110.9	O6—C16—C17	119.02 (12)
C2—C1—H1A	110.9	C15—C16—C17	119.00 (12)
O3—C1—H1B	110.9	O7—C17—C18	124.07 (13)
C2—C1—H1B	110.9	O7—C17—C16	115.16 (12)
H1A—C1—H1B	108.9	C18—C17—C16	120.77 (13)
C12—C2—C1	101.62 (11)	C13—C18—C17	120.00 (13)
C12—C2—C3	109.44 (12)	C13—C18—H18	120.0
C1—C2—C3	119.88 (12)	C17—C18—H18	120.0
C12—C2—H2	108.4	O5—C19—H19A	109.5
C1—C2—H2	108.4	O5—C19—H19B	109.5
C3—C2—H2	108.4	H19A—C19—H19B	109.5
N1—C3—C4	110.76 (12)	O5—C19—H19C	109.5
N1—C3—C2	110.88 (12)	H19A—C19—H19C	109.5
C4—C3—C2	109.56 (11)	H19B—C19—H19C	109.5
N1—C3—H3	108.5	O6—C20—H20A	109.5
C4—C3—H3	108.5	O6—C20—H20B	109.5
C2—C3—H3	108.5	H20A—C20—H20B	109.5
C10—C4—C5	120.25 (14)	O6—C20—H20C	109.5
C10—C4—C3	123.63 (13)	H20A—C20—H20C	109.5
C5—C4—C3	116.12 (13)	H20B—C20—H20C	109.5
C6—C5—C4	118.11 (14)	O7—C21—H21A	109.5
C6—C5—H5	120.9	O7—C21—H21B	109.5
C4—C5—H5	120.9	H21A—C21—H21B	109.5
C5—C6—O2	128.50 (14)	O7—C21—H21C	109.5
C5—C6—C8	121.80 (13)	H21A—C21—H21C	109.5
O2—C6—C8	109.61 (13)	H21B—C21—H21C	109.5
O2—C7—O1	107.52 (12)	N1—C22—C23	113.68 (12)
O2—C7—H7A	110.2	N1—C22—H22A	108.8
O1—C7—H7A	110.2	C23—C22—H22A	108.8
O2—C7—H7B	110.2	N1—C22—H22B	108.8
O1—C7—H7B	110.2	C23—C22—H22B	108.8
H7A—C7—H7B	108.5	H22A—C22—H22B	107.7
C9—C8—O1	128.67 (14)	C24—C23—C28	117.00 (13)
C9—C8—C6	121.71 (14)	C24—C23—C22	122.93 (13)
O1—C8—C6	109.61 (12)	C28—C23—C22	120.07 (13)
C8—C9—C10	118.03 (14)	C23—C24—C25	121.28 (14)
C8—C9—H9	121.0	C23—C24—H24	119.4
C10—C9—H9	121.0	C25—C24—H24	119.4
C4—C10—C9	120.05 (13)	C26—C25—C24	120.20 (14)
C4—C10—C11	122.78 (13)	C26—C25—H25	119.9
C9—C10—C11	117.17 (13)	C24—C25—H25	119.9
C10—C11—C13	113.17 (11)	C25—C26—C27	119.80 (14)
C10—C11—C12	107.35 (11)	C25—C26—H26	120.1
C13—C11—C12	113.84 (12)	C27—C26—H26	120.1
C10—C11—H11	107.4	C28—C27—C26	119.09 (14)
C13—C11—H11	107.4	C28—C27—H27	120.5
C12—C11—H11	107.4	C26—C27—H27	120.5
C30—C12—C2	103.68 (12)	C27—C28—C23	122.56 (14)
C30—C12—C11	120.93 (12)	C27—C28—Cl1	118.38 (12)
C2—C12—C11	110.93 (11)	C23—C28—Cl1	119.05 (11)
C30—C12—H12	106.8	O4—C30—O3	121.09 (14)
C2—C12—H12	106.8	O4—C30—C12	129.53 (15)
C11—C12—H12	106.8	O3—C30—C12	109.32 (13)

C30—O3—C1—C2	−23.55 (15)	C10—C11—C13—C14	−158.29 (13)
O3—C1—C2—C12	32.23 (14)	C12—C11—C13—C14	78.78 (17)
O3—C1—C2—C3	152.89 (12)	C10—C11—C13—C18	21.3 (2)
C22—N1—C3—C4	−138.33 (13)	C12—C11—C13—C18	−101.68 (15)
C22—N1—C3—C2	99.82 (14)	C18—C13—C14—C15	0.6 (2)
C12—C2—C3—N1	76.31 (15)	C11—C13—C14—C15	−179.85 (13)
C1—C2—C3—N1	−40.37 (18)	C19—O5—C15—C16	174.55 (13)
C12—C2—C3—C4	−46.24 (14)	C19—O5—C15—C14	−7.0 (2)
C1—C2—C3—C4	−162.92 (13)	C13—C14—C15—O5	−179.86 (13)
N1—C3—C4—C10	−111.37 (14)	C13—C14—C15—C16	−1.5 (2)
C2—C3—C4—C10	11.25 (18)	C20—O6—C16—C15	−71.65 (18)
N1—C3—C4—C5	68.97 (15)	C20—O6—C16—C17	113.25 (15)
C2—C3—C4—C5	−168.41 (12)	O5—C15—C16—O6	4.9 (2)
C10—C4—C5—C6	−1.1 (2)	C14—C15—C16—O6	−173.55 (13)
C3—C4—C5—C6	178.52 (12)	O5—C15—C16—C17	−179.98 (12)
C4—C5—C6—O2	−177.04 (14)	C14—C15—C16—C17	1.5 (2)
C4—C5—C6—C8	−0.8 (2)	C21—O7—C17—C18	−9.0 (2)
C7—O2—C6—C5	−171.48 (15)	C21—O7—C17—C16	170.60 (13)
C7—O2—C6—C8	11.94 (16)	O6—C16—C17—O7	−5.1 (2)
C6—O2—C7—O1	−19.05 (16)	C15—C16—C17—O7	179.68 (13)
C8—O1—C7—O2	18.94 (16)	O6—C16—C17—C18	174.50 (13)
C7—O1—C8—C9	169.91 (16)	C15—C16—C17—C18	−0.7 (2)
C7—O1—C8—C6	−11.63 (15)	C14—C13—C18—C17	0.2 (2)
C5—C6—C8—C9	1.6 (2)	C11—C13—C18—C17	−179.31 (13)
O2—C6—C8—C9	178.41 (13)	O7—C17—C18—C13	179.40 (13)
C5—C6—C8—O1	−177.03 (13)	C16—C17—C18—C13	−0.1 (2)
O2—C6—C8—O1	−0.17 (16)	C3—N1—C22—C23	−152.51 (12)
O1—C8—C9—C10	178.05 (13)	N1—C22—C23—C24	0.2 (2)
C6—C8—C9—C10	−0.2 (2)	N1—C22—C23—C28	179.56 (13)
C5—C4—C10—C9	2.4 (2)	C28—C23—C24—C25	−0.7 (2)
C3—C4—C10—C9	−177.21 (13)	C22—C23—C24—C25	178.61 (14)
C5—C4—C10—C11	−176.76 (13)	C23—C24—C25—C26	−1.5 (2)
C3—C4—C10—C11	3.6 (2)	C24—C25—C26—C27	2.1 (2)
C8—C9—C10—C4	−1.7 (2)	C25—C26—C27—C28	−0.4 (2)
C8—C9—C10—C11	177.53 (13)	C26—C27—C28—C23	−2.0 (2)
C4—C10—C11—C13	−109.51 (15)	C26—C27—C28—Cl1	176.65 (11)
C9—C10—C11—C13	71.28 (17)	C24—C23—C28—C27	2.5 (2)
C4—C10—C11—C12	16.95 (18)	C22—C23—C28—C27	−176.88 (13)
C9—C10—C11—C12	−162.27 (12)	C24—C23—C28—Cl1	−176.10 (11)
C1—C2—C12—C30	−29.50 (14)	C22—C23—C28—Cl1	4.52 (18)
C3—C2—C12—C30	−157.22 (11)	C1—O3—C30—O4	−173.15 (13)
C1—C2—C12—C11	−160.76 (12)	C1—O3—C30—C12	4.19 (15)
C3—C2—C12—C11	71.52 (14)	C2—C12—C30—O4	−166.14 (15)
C10—C11—C12—C30	−174.77 (13)	C11—C12—C30—O4	−41.1 (2)
C13—C11—C12—C30	−48.71 (18)	C2—C12—C30—O3	16.81 (14)
C10—C11—C12—C2	−53.14 (15)	C11—C12—C30—O3	141.88 (13)
C13—C11—C12—C2	72.92 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O7ⁱ	0.95	2.56	3.2130 (18)	126

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₈ClNO₇
M_r	537.97
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	113
a, b, c (Å)	10.0971 (14), 15.264 (2), 16.220 (2)
V (Å³)	2499.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.960, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	26247, 5968, 5580
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.066, 1.03
No. of reflections	5968
No. of parameters	350
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.25
Absolute structure	Flack (1983), 2615 Friedel pairs
Absolute structure parameter	0.00 (4)

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
C26—H26···O7ⁱ	0.95	2.56	3.2130 (18)	126.4

Symmetry code: (i) x, y−1, z.

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
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
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
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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Volume 67| Part 6| June 2011| Page o1491

doi:10.1107/S1600536811018289

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

9-[(2-Chloro­benz­yl)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-[(2-Chlorobenzyl)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