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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-Des­­oxy-4β-[(5-meth­­oxy-1H-indol-3-yl)oxalylamino]podophyllotoxin methanol solvate

aSchool of Pharmaceutical Sciences, Tianjin Medical University, Tianjin 300071, People's Republic of China, and bRoom of Pharmacognosy, Medical College of Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China
*Correspondence e-mail: chenhongtian06@yahoo.com.cn

(Received 18 September 2008; accepted 29 October 2008; online 13 November 2008)

The main mol­ecule of the title solvate, C33H30N2O10·CH3OH, is a new anti­tumor agent, which shows cytotoxicity against MDR cancer cell lines. It has been synthesized by coupling 4β-amino­podophyllotoxin with (5-meth­oxy-1H-indol-3-yl)glyoxyl chloride and structurally characterized. There are two crystallographically independent mol­ecules in the asymmetric unit, which differ in the dihedral angles between the aromatic rings. The dihedral angles between the benzene ring of the benzo[d][1,3]dioxole and the benzene ring of the 5-meth­oxy-1H-indole are 85.08 (3) and 76.88 (3)° and reflect the main conformational difference between the two independent mol­ecules. The asymmetric unit is completed with two methanol solvent mol­ecules, one of which is disordered over two positions, with occupancies close to 0.5.

Related literature

For related preparation and anti­tumor activity, see: 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.]); Knaack et al. (2001[Knaack, M., Emig, P., Bats, J. W., Kiesel, M., Muller, A. & Gunther, E. (2001). Eur. J. Org. Chem. pp. 3843-3847.]); Zhou et al. (1991[Zhou, X. M., Wang, Z. Q., Chang, J. Y., Chen, H. X., Cheng, Y. C. & Lee, K. H. (1991). J. Med. Chem. 34, 3346-3350.]); Zhu et al. (1999[Zhu, X.-K., Guan, J., Tachibana, Y., Bastow, K. F., Cho, S. J., Cheng, H.-H., Cheng, Y. C., Gurwith, M. & Lee, K.-H. (1999). J. Med. Chem. 42, 2441-2446.]); Chen et al. (2006[Chen, X., Liang, J. & Shang, Z.-C. (2006). Acta Cryst. E62, o3810-o3811.]).

[Scheme 1]

Experimental

Crystal data
  • C33H30N2O10·CH4O

  • Mr = 646.63

  • Monoclinic, P 21

  • a = 12.228 (2) Å

  • b = 9.8360 (16) Å

  • c = 26.667 (5) Å

  • β = 95.58 (3)°

  • V = 3192.2 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 113 (2) K

  • 0.24 × 0.22 × 0.12 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan, and MSC, The Woodlands, Texas, USA.]) Tmin = 0.976, Tmax = 0.988

  • 22853 measured reflections

  • 7730 independent reflections

  • 6754 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.127

  • S = 1.03

  • 7730 reflections

  • 893 parameters

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

  • Δρmax = 0.73 e Å−3

  • Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan, and MSC, The Woodlands, Texas, USA.]); 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

Podophyllotoxins are a particularly instructive class of compounds for consideration in the design and synthesis of potential anticancer agents based upon natural products prototypes. We present here the crystal structure of the title compound (Fig. 1), which can be used as a precursor for antitumor molecules. In the crystal structure, two crystallographically independent molecules are found in the asymmetric unit. The mean planes for the three benzene rings of benzo[d][1,3]dioxole (ring A), 3,4,5-trimethoxyphenyl (ring B) and 5-methoxy-1H-indole (ring C), form dihedral angles A/B = 88.00 (3) and 83.26 (3)°, B/C = 44.66 (3) and 50.01 (4)°, and A/C = 85.08 (3)/76.88 (3)°, respectively. This makes clear that the main difference between conformations in both independent molecules arises from A and C rings (dihedral angles differ by more than 8°), while the podophyllotoxin core structure remains more or less rigid.

Related literature top

For related preparation and antitumor activity, see: Yu et al. (2008); Knaack et al. (2001); Zhou et al. (1991); Zhu et al. (1999); Chen et al. (2006).

Experimental top

4β-Aminopodophyllotoxin (1.0 mmol), 5-methoxy-indol-3-yl-glyoxyl chloride (1.0 mmol) and Et3N (2.0 mmol) were dissolved in dry dichloromethane. The mixture was stirred at room temperature for 36 h., and then extracted with dichloromethane after 30 ml water was added. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate as eluent. Single crystals suitable for X-ray diffraction were prepared by evaporation of a methanol solution of the product.

Refinement top

In absence of significant anomalous dispersion effects, Friedel pairs were merged. The absolute configuration was assigned by reference to the known configuration of the starting material. One methanol molecule is disordered over two positions, and corresponding site occupation factors were refined to 0.522 (5) and 0.478 (5). All H atoms of N—H groups were located in a difference map and refined freely. All H atoms for O—H groups were placed in idealized positions, with O—H bond lengths of 0.84 Å. Other H atoms were positioned geometrically and refined using a riding model, with C—H bond lengths in the range 0.95–0.99 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 main molecules, with atom labels and 50% probability displacement ellipsoids for non-H atoms. The crystal is a methanol solvate, with a 1:1 composition with respect to the main molecule. Solvent molecules were omitted.
4-Desoxy-4β-[(5-methoxy-1H-indol-3-yl)oxalylamino]podophyllotoxin methanol solvate top
Crystal data top
C33H30N2O10·CH4OF(000) = 1360
Mr = 646.63Dx = 1.345 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8161 reflections
a = 12.228 (2) Åθ = 1.7–27.5°
b = 9.8360 (16) ŵ = 0.10 mm1
c = 26.667 (5) ÅT = 113 K
β = 95.58 (3)°Plate, yellow
V = 3192.2 (9) Å30.24 × 0.22 × 0.12 mm
Z = 4
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
7730 independent reflections
Radiation source: rotating anode6754 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.045
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 1.5°
ω and ϕ scansh = 1515
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1211
Tmin = 0.976, Tmax = 0.988l = 3134
22853 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0825P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
7730 reflectionsΔρmax = 0.73 e Å3
893 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0201 (14)
Primary atom site location: structure-invariant direct methods
Crystal data top
C33H30N2O10·CH4OV = 3192.2 (9) Å3
Mr = 646.63Z = 4
Monoclinic, P21Mo Kα radiation
a = 12.228 (2) ŵ = 0.10 mm1
b = 9.8360 (16) ÅT = 113 K
c = 26.667 (5) Å0.24 × 0.22 × 0.12 mm
β = 95.58 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
7730 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
6754 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.988Rint = 0.045
22853 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.73 e Å3
7730 reflectionsΔρmin = 0.27 e Å3
893 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.9709 (2)0.2102 (3)0.43373 (9)0.0355 (6)
O20.83051 (16)0.5566 (2)0.29071 (8)0.0237 (5)
O30.56989 (19)0.5637 (3)0.22380 (9)0.0430 (7)
O40.7776 (2)1.1791 (3)0.23313 (9)0.0381 (6)
O50.89806 (19)1.2324 (3)0.17487 (9)0.0344 (6)
O60.74319 (19)0.4426 (2)0.07044 (9)0.0318 (5)
O70.8771 (2)0.5210 (2)0.02670 (9)0.0338 (5)
O80.51000 (18)1.0135 (3)0.01957 (8)0.0303 (5)
O90.59367 (17)0.9543 (2)0.10683 (8)0.0251 (5)
O100.79144 (17)0.8430 (3)0.10779 (8)0.0285 (5)
O111.10961 (19)0.6741 (2)0.06729 (8)0.0293 (5)
O120.96392 (17)0.7624 (2)0.23470 (8)0.0252 (5)
O131.0023 (2)1.0455 (3)0.31461 (8)0.0324 (5)
O140.45644 (19)0.9379 (3)0.28103 (9)0.0392 (6)
O150.39852 (17)0.7404 (3)0.31787 (9)0.0350 (6)
O161.05011 (18)0.7382 (3)0.45386 (8)0.0312 (5)
O170.97883 (19)0.5355 (2)0.47195 (8)0.0296 (5)
O180.59318 (19)0.8892 (2)0.55775 (8)0.0273 (5)
O190.61900 (16)0.6673 (2)0.61567 (7)0.0238 (5)
O200.7020 (2)0.4377 (2)0.58168 (8)0.0319 (5)
N10.5534 (2)0.3107 (3)0.34849 (10)0.0280 (6)
H10.490 (3)0.275 (4)0.3584 (14)0.034*
N20.7327 (2)0.6542 (3)0.20608 (9)0.0229 (5)
H20.812 (3)0.671 (4)0.2177 (13)0.027*
N31.2084 (2)1.0934 (3)0.19960 (10)0.0249 (6)
H3A1.252 (3)1.166 (4)0.2089 (14)0.030*
N40.8928 (2)0.8590 (3)0.31837 (9)0.0212 (5)
H4A0.865 (3)0.788 (4)0.3026 (13)0.025*
C11.0619 (3)0.2694 (4)0.41211 (13)0.0358 (8)
H1A1.06010.24240.37670.054*
H1B1.13060.23790.43040.054*
H1C1.05760.36870.41440.054*
C20.8683 (3)0.2420 (3)0.41280 (12)0.0261 (7)
C30.7839 (3)0.1797 (3)0.43615 (12)0.0294 (7)
H30.80150.12540.46530.035*
C40.6750 (3)0.1962 (3)0.41739 (12)0.0292 (7)
H40.61730.15320.43290.035*
C50.6535 (3)0.2779 (3)0.37513 (11)0.0242 (6)
C60.5696 (3)0.3946 (3)0.31033 (11)0.0262 (7)
H60.51340.43010.28690.031*
C70.6824 (2)0.4218 (3)0.31032 (11)0.0216 (6)
C80.7367 (2)0.3440 (3)0.35189 (10)0.0200 (6)
C90.8474 (2)0.3262 (3)0.37056 (11)0.0232 (6)
H90.90520.36930.35520.028*
C100.7340 (2)0.5197 (3)0.28133 (10)0.0202 (6)
C110.6682 (2)0.5823 (3)0.23466 (11)0.0252 (7)
C120.6859 (2)0.7245 (3)0.16045 (11)0.0238 (6)
H120.60600.74000.16340.029*
C130.6968 (2)0.6420 (3)0.11236 (11)0.0227 (6)
H130.64320.67940.08510.027*
C140.6835 (3)0.4872 (4)0.11279 (13)0.0305 (7)
H14A0.71630.44790.14500.037*
H14B0.60510.46100.10750.037*
C150.8175 (3)0.5382 (3)0.05986 (12)0.0268 (7)
C160.8111 (2)0.6562 (3)0.09543 (10)0.0211 (6)
H160.86420.63680.12550.025*
C170.8347 (2)0.8009 (3)0.07850 (10)0.0195 (6)
H170.91440.80650.07320.023*
C180.8143 (2)0.8956 (3)0.12187 (11)0.0209 (6)
C190.8700 (2)1.0211 (3)0.12473 (11)0.0236 (6)
H190.91811.04610.10040.028*
C200.8522 (2)1.1066 (3)0.16423 (12)0.0254 (6)
C210.8708 (3)1.2608 (4)0.22494 (13)0.0362 (8)
H21A0.93341.23810.24990.043*
H21B0.85311.35840.22840.043*
C220.7809 (3)1.0735 (3)0.19899 (12)0.0278 (7)
C230.7237 (2)0.9546 (4)0.19687 (11)0.0260 (7)
H230.67330.93440.22080.031*
C240.7416 (2)0.8628 (3)0.15812 (10)0.0222 (6)
C250.7684 (2)0.8429 (3)0.02942 (10)0.0196 (6)
C260.6673 (2)0.9084 (3)0.02973 (11)0.0225 (6)
H260.63830.92710.06080.027*
C270.6086 (2)0.9465 (3)0.01582 (11)0.0225 (6)
C280.6521 (2)0.9191 (3)0.06129 (11)0.0233 (6)
C290.7545 (2)0.8577 (3)0.06123 (11)0.0213 (6)
C300.8123 (2)0.8184 (3)0.01594 (11)0.0226 (6)
H300.88160.77480.01600.027*
C310.4672 (3)1.0519 (5)0.02636 (14)0.0418 (9)
H31A0.45440.97020.04600.063*
H31B0.39781.10080.01870.063*
H31C0.52021.11090.04590.063*
C320.6137 (3)1.0929 (4)0.12153 (14)0.0344 (8)
H32A0.58771.15540.09670.052*
H32B0.57441.11090.15470.052*
H32C0.69271.10630.12320.052*
C330.9057 (3)0.8143 (5)0.10879 (13)0.0363 (8)
H33A0.94910.88240.08880.054*
H33B0.92450.81700.14370.054*
H33C0.92180.72370.09460.054*
C341.1325 (3)0.6781 (4)0.01564 (12)0.0318 (7)
H34A1.11130.76700.00120.048*
H34B1.09060.60660.00320.048*
H34C1.21120.66340.01360.048*
C351.1422 (2)0.7832 (3)0.09760 (11)0.0228 (6)
C361.2157 (2)0.8833 (3)0.08386 (12)0.0256 (6)
H361.24490.87790.05220.031*
C371.2456 (3)0.9898 (3)0.11633 (12)0.0268 (7)
H371.29591.05750.10760.032*
C381.1995 (2)0.9946 (3)0.16239 (11)0.0235 (6)
C391.1422 (2)1.0624 (3)0.23537 (11)0.0220 (6)
H391.13371.11590.26440.026*
C401.0877 (2)0.9400 (3)0.22359 (11)0.0208 (6)
C411.1253 (2)0.8955 (3)0.17615 (11)0.0196 (6)
C421.0986 (2)0.7857 (3)0.14365 (11)0.0214 (6)
H421.05170.71480.15300.026*
C431.0061 (2)0.8723 (3)0.24936 (10)0.0206 (6)
C440.9674 (2)0.9361 (3)0.29783 (10)0.0216 (6)
C450.8387 (2)0.9029 (3)0.36257 (10)0.0218 (6)
H450.84021.00440.36440.026*
C460.8942 (2)0.8449 (3)0.41195 (11)0.0221 (6)
H460.85860.88600.44060.027*
C471.0178 (3)0.8571 (4)0.42313 (12)0.0289 (7)
H47A1.05420.85670.39160.035*
H47B1.03750.94200.44180.035*
C480.9684 (3)0.6421 (3)0.45032 (11)0.0254 (7)
C490.8766 (2)0.6920 (3)0.41273 (11)0.0216 (6)
H490.89440.65810.37910.026*
C500.7568 (2)0.6525 (3)0.41697 (10)0.0210 (6)
H500.74860.55580.40570.025*
C510.6837 (2)0.7376 (3)0.37934 (10)0.0208 (6)
C520.5740 (2)0.6926 (3)0.36810 (11)0.0235 (6)
H520.54840.61290.38340.028*
C530.5061 (2)0.7661 (3)0.33488 (12)0.0257 (7)
C540.3728 (4)0.8367 (6)0.2790 (2)0.0734 (17)
H54A0.30100.87960.28320.088*
H54B0.36730.79060.24580.088*
C550.5417 (3)0.8846 (4)0.31276 (12)0.0284 (7)
C560.6461 (2)0.9325 (3)0.32251 (11)0.0247 (6)
H560.66911.01400.30760.030*
C570.7191 (2)0.8550 (3)0.35611 (10)0.0203 (6)
C580.7206 (2)0.6588 (3)0.47014 (11)0.0202 (6)
C590.6749 (2)0.7768 (3)0.48856 (11)0.0216 (6)
H590.66640.85540.46790.026*
C600.6418 (2)0.7796 (3)0.53700 (11)0.0197 (6)
C610.6544 (2)0.6648 (3)0.56788 (11)0.0207 (6)
C620.6964 (2)0.5457 (3)0.54896 (11)0.0212 (6)
C630.7300 (2)0.5425 (3)0.50054 (11)0.0235 (6)
H630.75950.46120.48810.028*
C640.5741 (3)1.0045 (3)0.52584 (13)0.0303 (7)
H64A0.64461.04260.51820.045*
H64B0.53311.07320.54290.045*
H64C0.53150.97700.49450.045*
C650.7057 (3)0.6693 (6)0.65580 (12)0.0495 (12)
H65A0.75800.59630.65080.074*
H65B0.67480.65590.68800.074*
H65C0.74350.75720.65610.074*
C660.6889 (3)0.3055 (3)0.55972 (13)0.0300 (7)
H66A0.62290.30400.53580.045*
H66B0.68160.23820.58630.045*
H66C0.75340.28370.54210.045*
O210.3925 (2)0.2634 (4)0.18772 (15)0.0800 (13)
H210.38690.32510.16590.120*
C670.4991 (4)0.2072 (5)0.19056 (18)0.0584 (13)
H67A0.55360.27960.19740.088*
H67B0.51030.16310.15850.088*
H67C0.50750.13990.21780.088*
O220.1884 (6)0.3747 (4)0.24506 (19)0.0478 (17)0.522 (5)
H220.13010.39320.25790.072*0.522 (5)
C680.2343 (10)0.4948 (7)0.2278 (3)0.065 (3)0.522 (5)
H68A0.18540.57150.23280.097*0.522 (5)
H68B0.24370.48590.19190.097*0.522 (5)
H68C0.30600.51080.24670.097*0.522 (5)
O230.0596 (3)0.4971 (5)0.3106 (2)0.0326 (13)0.478 (5)
H23A0.07920.48530.28160.049*0.478 (5)
C690.1315 (5)0.5923 (8)0.3374 (3)0.0304 (16)0.478 (5)
H69A0.13700.67430.31690.046*0.478 (5)
H69B0.20450.55160.34440.046*0.478 (5)
H69C0.10240.61640.36910.046*0.478 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0363 (13)0.0429 (14)0.0266 (13)0.0155 (12)0.0001 (10)0.0051 (10)
O20.0213 (10)0.0284 (11)0.0208 (11)0.0039 (9)0.0014 (8)0.0040 (9)
O30.0254 (11)0.0656 (19)0.0363 (14)0.0155 (12)0.0068 (10)0.0265 (13)
O40.0387 (13)0.0425 (15)0.0340 (14)0.0010 (12)0.0082 (10)0.0162 (12)
O50.0371 (13)0.0304 (12)0.0361 (14)0.0064 (11)0.0060 (10)0.0111 (11)
O60.0366 (12)0.0269 (12)0.0304 (12)0.0036 (11)0.0037 (10)0.0030 (10)
O70.0407 (13)0.0297 (13)0.0307 (13)0.0034 (11)0.0017 (10)0.0055 (10)
O80.0249 (11)0.0442 (14)0.0213 (11)0.0112 (10)0.0004 (8)0.0018 (10)
O90.0253 (10)0.0310 (12)0.0175 (10)0.0014 (10)0.0055 (8)0.0018 (9)
O100.0259 (11)0.0428 (13)0.0172 (11)0.0039 (10)0.0034 (8)0.0004 (10)
O110.0388 (12)0.0294 (12)0.0207 (11)0.0006 (10)0.0074 (9)0.0050 (9)
O120.0261 (10)0.0260 (11)0.0244 (11)0.0060 (9)0.0068 (8)0.0036 (9)
O130.0405 (13)0.0311 (12)0.0271 (12)0.0126 (11)0.0110 (10)0.0063 (10)
O140.0284 (12)0.0488 (16)0.0386 (14)0.0029 (12)0.0063 (10)0.0109 (12)
O150.0224 (11)0.0519 (16)0.0297 (12)0.0015 (11)0.0033 (9)0.0046 (11)
O160.0275 (11)0.0417 (13)0.0235 (12)0.0037 (11)0.0026 (9)0.0051 (10)
O170.0359 (12)0.0297 (12)0.0229 (11)0.0067 (10)0.0019 (9)0.0017 (10)
O180.0383 (12)0.0229 (11)0.0221 (11)0.0075 (10)0.0099 (9)0.0011 (9)
O190.0262 (10)0.0305 (11)0.0155 (10)0.0048 (9)0.0063 (8)0.0044 (9)
O200.0516 (14)0.0228 (11)0.0225 (11)0.0046 (11)0.0091 (10)0.0051 (9)
N10.0249 (13)0.0355 (16)0.0239 (14)0.0089 (12)0.0031 (10)0.0049 (11)
N20.0196 (12)0.0315 (14)0.0170 (12)0.0044 (11)0.0013 (9)0.0077 (11)
N30.0254 (12)0.0260 (14)0.0231 (13)0.0092 (12)0.0013 (10)0.0005 (10)
N40.0240 (12)0.0241 (13)0.0161 (12)0.0037 (11)0.0043 (9)0.0018 (10)
C10.0304 (17)0.046 (2)0.0301 (18)0.0113 (16)0.0041 (13)0.0047 (16)
C20.0342 (16)0.0246 (15)0.0193 (15)0.0072 (14)0.0015 (12)0.0019 (12)
C30.0482 (19)0.0238 (16)0.0170 (15)0.0076 (15)0.0075 (13)0.0025 (12)
C40.0441 (18)0.0257 (17)0.0188 (15)0.0033 (15)0.0088 (13)0.0027 (12)
C50.0305 (15)0.0228 (15)0.0197 (15)0.0030 (13)0.0039 (12)0.0003 (12)
C60.0257 (15)0.0341 (17)0.0186 (15)0.0069 (14)0.0016 (11)0.0053 (13)
C70.0228 (14)0.0240 (15)0.0181 (14)0.0034 (13)0.0022 (11)0.0013 (11)
C80.0291 (15)0.0165 (13)0.0149 (13)0.0001 (12)0.0041 (11)0.0022 (11)
C90.0262 (14)0.0200 (15)0.0237 (15)0.0009 (13)0.0042 (12)0.0033 (12)
C100.0197 (13)0.0250 (15)0.0161 (13)0.0026 (12)0.0032 (10)0.0014 (11)
C110.0256 (14)0.0327 (17)0.0164 (14)0.0040 (13)0.0014 (11)0.0047 (12)
C120.0220 (14)0.0313 (16)0.0174 (14)0.0017 (13)0.0018 (11)0.0056 (12)
C130.0226 (14)0.0270 (16)0.0176 (14)0.0034 (12)0.0034 (11)0.0043 (12)
C140.0326 (16)0.0294 (17)0.0283 (17)0.0092 (14)0.0035 (13)0.0062 (14)
C150.0291 (15)0.0239 (15)0.0261 (16)0.0025 (14)0.0048 (12)0.0012 (13)
C160.0217 (13)0.0251 (15)0.0158 (14)0.0011 (12)0.0021 (11)0.0003 (11)
C170.0186 (13)0.0243 (15)0.0155 (13)0.0008 (12)0.0011 (10)0.0017 (11)
C180.0214 (13)0.0237 (15)0.0171 (14)0.0025 (12)0.0004 (11)0.0012 (11)
C190.0228 (14)0.0256 (16)0.0228 (15)0.0012 (13)0.0034 (11)0.0012 (12)
C200.0238 (14)0.0262 (15)0.0257 (16)0.0005 (13)0.0007 (12)0.0015 (12)
C210.0429 (19)0.0313 (18)0.0336 (19)0.0021 (16)0.0002 (15)0.0104 (15)
C220.0292 (16)0.0317 (18)0.0227 (16)0.0057 (14)0.0023 (12)0.0073 (13)
C230.0262 (15)0.0341 (18)0.0185 (15)0.0001 (14)0.0059 (11)0.0024 (13)
C240.0209 (13)0.0307 (16)0.0146 (13)0.0008 (13)0.0001 (10)0.0013 (12)
C250.0225 (13)0.0193 (14)0.0165 (13)0.0008 (12)0.0006 (10)0.0010 (11)
C260.0221 (13)0.0251 (15)0.0203 (14)0.0006 (12)0.0021 (11)0.0021 (12)
C270.0190 (13)0.0268 (16)0.0214 (14)0.0001 (12)0.0003 (11)0.0016 (12)
C280.0242 (14)0.0257 (15)0.0189 (14)0.0008 (13)0.0036 (11)0.0006 (12)
C290.0241 (14)0.0241 (15)0.0161 (13)0.0006 (13)0.0039 (10)0.0029 (11)
C300.0195 (13)0.0256 (16)0.0222 (15)0.0008 (12)0.0006 (11)0.0008 (12)
C310.0315 (18)0.065 (3)0.0295 (18)0.0187 (19)0.0044 (14)0.0022 (18)
C320.0369 (18)0.0341 (19)0.0296 (18)0.0012 (15)0.0102 (14)0.0079 (14)
C330.0264 (16)0.060 (2)0.0233 (17)0.0033 (17)0.0080 (12)0.0068 (16)
C340.0459 (19)0.0319 (17)0.0177 (15)0.0054 (16)0.0036 (13)0.0037 (13)
C350.0236 (14)0.0237 (15)0.0211 (15)0.0034 (13)0.0020 (11)0.0009 (12)
C360.0262 (15)0.0294 (17)0.0221 (15)0.0008 (13)0.0067 (12)0.0020 (13)
C370.0271 (15)0.0299 (16)0.0244 (16)0.0056 (14)0.0078 (12)0.0037 (13)
C380.0220 (14)0.0267 (15)0.0217 (15)0.0021 (12)0.0019 (11)0.0022 (12)
C390.0203 (13)0.0276 (16)0.0177 (14)0.0021 (12)0.0003 (10)0.0015 (12)
C400.0208 (13)0.0240 (15)0.0168 (13)0.0014 (12)0.0014 (10)0.0012 (11)
C410.0156 (12)0.0231 (15)0.0204 (14)0.0018 (11)0.0025 (10)0.0019 (11)
C420.0180 (13)0.0259 (15)0.0202 (15)0.0014 (12)0.0019 (10)0.0015 (12)
C430.0217 (13)0.0247 (15)0.0156 (13)0.0017 (12)0.0021 (10)0.0007 (11)
C440.0225 (13)0.0266 (15)0.0154 (13)0.0004 (13)0.0009 (10)0.0002 (12)
C450.0261 (14)0.0243 (15)0.0158 (14)0.0039 (12)0.0063 (11)0.0011 (11)
C460.0248 (14)0.0271 (15)0.0152 (14)0.0017 (13)0.0054 (11)0.0000 (11)
C470.0296 (16)0.0368 (18)0.0199 (15)0.0076 (15)0.0001 (12)0.0021 (13)
C480.0251 (14)0.0316 (18)0.0200 (15)0.0035 (13)0.0041 (11)0.0053 (13)
C490.0214 (14)0.0276 (16)0.0159 (14)0.0001 (12)0.0019 (11)0.0037 (11)
C500.0255 (14)0.0217 (15)0.0160 (14)0.0001 (12)0.0024 (11)0.0005 (11)
C510.0241 (14)0.0257 (15)0.0129 (13)0.0001 (13)0.0042 (11)0.0038 (11)
C520.0241 (14)0.0275 (16)0.0196 (15)0.0009 (13)0.0059 (11)0.0009 (12)
C530.0216 (14)0.0338 (17)0.0220 (15)0.0028 (13)0.0041 (11)0.0039 (13)
C540.045 (2)0.072 (3)0.096 (4)0.017 (2)0.029 (2)0.045 (3)
C550.0277 (15)0.0354 (18)0.0212 (15)0.0058 (14)0.0026 (12)0.0018 (13)
C560.0309 (15)0.0264 (16)0.0173 (14)0.0005 (14)0.0051 (11)0.0001 (12)
C570.0217 (13)0.0249 (15)0.0143 (13)0.0004 (12)0.0023 (10)0.0035 (11)
C580.0209 (13)0.0212 (14)0.0189 (14)0.0041 (12)0.0029 (11)0.0007 (11)
C590.0251 (14)0.0201 (14)0.0193 (14)0.0004 (12)0.0010 (11)0.0020 (11)
C600.0169 (12)0.0225 (15)0.0196 (14)0.0013 (12)0.0018 (10)0.0039 (12)
C610.0188 (13)0.0277 (15)0.0159 (13)0.0012 (12)0.0036 (10)0.0002 (12)
C620.0235 (14)0.0200 (14)0.0200 (14)0.0000 (12)0.0012 (11)0.0048 (12)
C630.0264 (15)0.0207 (14)0.0234 (15)0.0010 (13)0.0024 (11)0.0017 (12)
C640.0374 (17)0.0230 (16)0.0319 (18)0.0067 (14)0.0108 (14)0.0035 (13)
C650.0361 (18)0.099 (4)0.0131 (16)0.017 (2)0.0003 (13)0.0042 (19)
C660.0288 (16)0.0245 (16)0.0369 (19)0.0046 (14)0.0040 (13)0.0034 (14)
O210.0418 (16)0.083 (3)0.109 (3)0.0281 (18)0.0256 (17)0.069 (2)
C670.051 (2)0.062 (3)0.060 (3)0.007 (2)0.011 (2)0.027 (2)
O220.095 (5)0.017 (2)0.034 (3)0.002 (3)0.022 (3)0.0010 (19)
C680.141 (10)0.025 (4)0.031 (4)0.021 (5)0.019 (5)0.005 (3)
O230.0067 (19)0.039 (3)0.053 (3)0.0004 (19)0.0034 (19)0.008 (2)
C690.022 (3)0.040 (4)0.030 (4)0.005 (3)0.005 (3)0.009 (3)
Geometric parameters (Å, º) top
O1—C21.359 (4)C26—C271.400 (4)
O1—C11.426 (5)C26—H260.9500
O2—C101.236 (3)C27—C281.397 (4)
O3—C111.223 (4)C28—C291.390 (4)
O4—C221.384 (4)C29—C301.393 (4)
O4—C211.428 (4)C30—H300.9500
O5—C201.377 (4)C31—H31A0.9800
O5—C211.435 (4)C31—H31B0.9800
O6—C151.356 (4)C31—H31C0.9800
O6—C141.470 (4)C32—H32A0.9800
O7—C151.212 (4)C32—H32B0.9800
O8—C271.370 (4)C32—H32C0.9800
O8—C311.429 (4)C33—H33A0.9800
O9—C281.392 (3)C33—H33B0.9800
O9—C321.446 (4)C33—H33C0.9800
O10—C291.369 (3)C34—H34A0.9800
O10—C331.428 (4)C34—H34B0.9800
O11—C351.379 (4)C34—H34C0.9800
O11—C341.432 (4)C35—C421.386 (4)
O12—C431.244 (4)C35—C361.405 (4)
O13—C441.226 (4)C36—C371.386 (5)
O14—C551.380 (4)C36—H360.9500
O14—C541.425 (5)C37—C381.401 (4)
O15—C531.373 (4)C37—H370.9500
O15—C541.417 (5)C38—C411.404 (4)
O16—C481.372 (4)C39—C401.397 (4)
O16—C471.460 (4)C39—H390.9500
O17—C481.198 (4)C40—C431.430 (4)
O18—C601.373 (4)C40—C411.455 (4)
O18—C641.423 (4)C41—C421.404 (4)
O19—C611.385 (3)C42—H420.9500
O19—C651.431 (4)C43—C441.551 (4)
O20—C621.372 (4)C45—C571.530 (4)
O20—C661.429 (4)C45—C461.532 (4)
N1—C61.339 (4)C45—H451.0000
N1—C51.391 (4)C46—C471.516 (4)
N1—H10.92 (4)C46—C491.520 (4)
N2—C111.349 (4)C46—H461.0000
N2—C121.467 (4)C47—H47A0.9900
N2—H21.00 (4)C47—H47B0.9900
N3—C391.345 (4)C48—C491.512 (4)
N3—C381.386 (4)C49—C501.530 (4)
N3—H3A0.91 (4)C49—H491.0000
N4—C441.344 (4)C50—C581.527 (4)
N4—C451.471 (4)C50—C511.528 (4)
N4—H4A0.87 (4)C50—H501.0000
C1—H1A0.9800C51—C571.399 (4)
C1—H1B0.9800C51—C521.416 (4)
C1—H1C0.9800C52—C531.361 (4)
C2—C31.398 (5)C52—H520.9500
C2—C91.402 (4)C53—C551.395 (5)
C3—C41.386 (5)C54—H54A0.9900
C3—H30.9500C54—H54B0.9900
C4—C51.388 (4)C55—C561.362 (4)
C4—H40.9500C56—C571.423 (4)
C5—C81.402 (4)C56—H560.9500
C6—C71.406 (4)C58—C591.397 (4)
C6—H60.9500C58—C631.400 (4)
C7—C101.421 (4)C59—C601.391 (4)
C7—C81.453 (4)C59—H590.9500
C8—C91.407 (4)C60—C611.397 (4)
C9—H90.9500C61—C621.393 (4)
C10—C111.543 (4)C62—C631.393 (4)
C12—C241.525 (5)C63—H630.9500
C12—C131.534 (4)C64—H64A0.9800
C12—H121.0000C64—H64B0.9800
C13—C161.517 (4)C64—H64C0.9800
C13—C141.531 (5)C65—H65A0.9800
C13—H131.0000C65—H65B0.9800
C14—H14A0.9900C65—H65C0.9800
C14—H14B0.9900C66—H66A0.9800
C15—C161.506 (4)C66—H66B0.9800
C16—C171.529 (4)C66—H66C0.9800
C16—H161.0000O21—C671.411 (6)
C17—C181.524 (4)O21—H210.8400
C17—C251.528 (4)C67—H67A0.9800
C17—H171.0000C67—H67B0.9800
C18—C191.408 (4)C67—H67C0.9800
C18—C241.412 (4)O22—C681.405 (7)
C19—C201.382 (4)O22—H220.8400
C19—H190.9500C68—H68A0.9800
C20—C221.372 (5)C68—H68B0.9800
C21—H21A0.9900C68—H68C0.9800
C21—H21B0.9900O23—C691.428 (7)
C22—C231.361 (5)O23—H23A0.8400
C23—C241.406 (4)C69—H69A0.9800
C23—H230.9500C69—H69B0.9800
C25—C301.391 (4)C69—H69C0.9800
C25—C261.395 (4)
C2—O1—C1117.7 (3)H33A—C33—H33C109.5
C22—O4—C21104.3 (2)H33B—C33—H33C109.5
C20—O5—C21103.9 (3)O11—C34—H34A109.5
C15—O6—C14110.2 (2)O11—C34—H34B109.5
C27—O8—C31117.2 (2)H34A—C34—H34B109.5
C28—O9—C32112.6 (2)O11—C34—H34C109.5
C29—O10—C33116.6 (2)H34A—C34—H34C109.5
C35—O11—C34118.0 (3)H34B—C34—H34C109.5
C55—O14—C54104.8 (3)O11—C35—C42114.7 (3)
C53—O15—C54104.9 (3)O11—C35—C36123.3 (3)
C48—O16—C47110.9 (2)C42—C35—C36122.0 (3)
C60—O18—C64115.9 (2)C37—C36—C35120.3 (3)
C61—O19—C65114.4 (2)C37—C36—H36119.9
C62—O20—C66116.6 (2)C35—C36—H36119.9
C6—N1—C5110.1 (3)C36—C37—C38117.9 (3)
C6—N1—H1130 (2)C36—C37—H37121.0
C5—N1—H1120 (2)C38—C37—H37121.0
C11—N2—C12120.9 (2)N3—C38—C37129.8 (3)
C11—N2—H2121 (2)N3—C38—C41107.9 (2)
C12—N2—H2118 (2)C37—C38—C41122.1 (3)
C39—N3—C38109.7 (3)N3—C39—C40110.1 (3)
C39—N3—H3A111 (2)N3—C39—H39125.0
C38—N3—H3A138 (2)C40—C39—H39125.0
C44—N4—C45122.5 (3)C39—C40—C43129.3 (3)
C44—N4—H4A121 (2)C39—C40—C41105.7 (3)
C45—N4—H4A116 (2)C43—C40—C41124.9 (3)
O1—C1—H1A109.5C38—C41—C42119.4 (3)
O1—C1—H1B109.5C38—C41—C40106.6 (3)
H1A—C1—H1B109.5C42—C41—C40133.9 (3)
O1—C1—H1C109.5C35—C42—C41118.2 (3)
H1A—C1—H1C109.5C35—C42—H42120.9
H1B—C1—H1C109.5C41—C42—H42120.9
O1—C2—C3114.1 (3)O12—C43—C40122.7 (3)
O1—C2—C9123.8 (3)O12—C43—C44117.6 (3)
C3—C2—C9122.1 (3)C40—C43—C44119.7 (3)
C4—C3—C2120.9 (3)O13—C44—N4125.0 (3)
C4—C3—H3119.6O13—C44—C43122.4 (3)
C2—C3—H3119.6N4—C44—C43112.7 (3)
C3—C4—C5117.4 (3)N4—C45—C57108.6 (2)
C3—C4—H4121.3N4—C45—C46112.6 (2)
C5—C4—H4121.3C57—C45—C46108.7 (2)
C4—C5—N1129.6 (3)N4—C45—H45109.0
C4—C5—C8122.6 (3)C57—C45—H45109.0
N1—C5—C8107.8 (3)C46—C45—H45109.0
N1—C6—C7109.6 (3)C47—C46—C49102.4 (3)
N1—C6—H6125.2C47—C46—C45119.3 (2)
C7—C6—H6125.2C49—C46—C45109.2 (2)
C6—C7—C10128.1 (3)C47—C46—H46108.5
C6—C7—C8105.9 (3)C49—C46—H46108.5
C10—C7—C8125.3 (3)C45—C46—H46108.5
C5—C8—C9120.0 (3)O16—C47—C46104.9 (2)
C5—C8—C7106.5 (3)O16—C47—H47A110.8
C9—C8—C7133.4 (3)C46—C47—H47A110.8
C2—C9—C8116.9 (3)O16—C47—H47B110.8
C2—C9—H9121.6C46—C47—H47B110.8
C8—C9—H9121.6H47A—C47—H47B108.8
O2—C10—C7123.7 (3)O17—C48—O16121.8 (3)
O2—C10—C11117.3 (3)O17—C48—C49129.8 (3)
C7—C10—C11119.0 (2)O16—C48—C49108.1 (3)
O3—C11—N2124.1 (3)C48—C49—C46103.5 (2)
O3—C11—C10123.7 (3)C48—C49—C50121.5 (3)
N2—C11—C10112.1 (2)C46—C49—C50113.0 (3)
N2—C12—C24108.4 (2)C48—C49—H49105.9
N2—C12—C13112.7 (3)C46—C49—H49105.9
C24—C12—C13111.3 (2)C50—C49—H49105.9
N2—C12—H12108.1C58—C50—C51112.5 (2)
C24—C12—H12108.1C58—C50—C49115.1 (2)
C13—C12—H12108.1C51—C50—C49108.4 (2)
C16—C13—C14101.3 (3)C58—C50—H50106.8
C16—C13—C12110.9 (2)C51—C50—H50106.8
C14—C13—C12120.1 (3)C49—C50—H50106.8
C16—C13—H13108.0C57—C51—C52119.5 (3)
C14—C13—H13108.0C57—C51—C50123.8 (3)
C12—C13—H13108.0C52—C51—C50116.7 (3)
O6—C14—C13103.3 (3)C53—C52—C51118.4 (3)
O6—C14—H14A111.1C53—C52—H52120.8
C13—C14—H14A111.1C51—C52—H52120.8
O6—C14—H14B111.1C52—C53—O15128.4 (3)
C13—C14—H14B111.1C52—C53—C55121.6 (3)
H14A—C14—H14B109.1O15—C53—C55110.0 (3)
O7—C15—O6121.2 (3)O15—C54—O14109.4 (3)
O7—C15—C16129.7 (3)O15—C54—H54A109.8
O6—C15—C16109.1 (3)O14—C54—H54A109.8
C15—C16—C13102.8 (2)O15—C54—H54B109.8
C15—C16—C17120.6 (2)O14—C54—H54B109.8
C13—C16—C17112.3 (2)H54A—C54—H54B108.3
C15—C16—H16106.8C56—C55—O14128.6 (3)
C13—C16—H16106.8C56—C55—C53122.2 (3)
C17—C16—H16106.8O14—C55—C53109.2 (3)
C18—C17—C25111.9 (2)C55—C56—C57117.0 (3)
C18—C17—C16107.2 (2)C55—C56—H56121.5
C25—C17—C16113.9 (2)C57—C56—H56121.5
C18—C17—H17107.9C51—C57—C56121.2 (3)
C25—C17—H17107.9C51—C57—C45122.6 (3)
C16—C17—H17107.9C56—C57—C45116.1 (3)
C19—C18—C24119.8 (3)C59—C58—C63119.2 (3)
C19—C18—C17117.5 (3)C59—C58—C50121.5 (3)
C24—C18—C17122.7 (3)C63—C58—C50119.3 (3)
C20—C19—C18117.6 (3)C60—C59—C58120.4 (3)
C20—C19—H19121.2C60—C59—H59119.8
C18—C19—H19121.2C58—C59—H59119.8
C22—C20—O5110.3 (3)O18—C60—C59124.5 (3)
C22—C20—C19121.9 (3)O18—C60—C61115.1 (2)
O5—C20—C19127.8 (3)C59—C60—C61120.4 (3)
O4—C21—O5107.1 (3)O19—C61—C62120.4 (3)
O4—C21—H21A110.3O19—C61—C60120.2 (3)
O5—C21—H21A110.3C62—C61—C60119.3 (3)
O4—C21—H21B110.3O20—C62—C63124.8 (3)
O5—C21—H21B110.3O20—C62—C61114.7 (3)
H21A—C21—H21B108.6C63—C62—C61120.5 (3)
C23—C22—C20122.2 (3)C62—C63—C58120.2 (3)
C23—C22—O4128.6 (3)C62—C63—H63119.9
C20—C22—O4109.1 (3)C58—C63—H63119.9
C22—C23—C24117.8 (3)O18—C64—H64A109.5
C22—C23—H23121.1O18—C64—H64B109.5
C24—C23—H23121.1H64A—C64—H64B109.5
C23—C24—C18120.6 (3)O18—C64—H64C109.5
C23—C24—C12116.2 (3)H64A—C64—H64C109.5
C18—C24—C12123.0 (3)H64B—C64—H64C109.5
C30—C25—C26120.2 (3)O19—C65—H65A109.5
C30—C25—C17118.7 (3)O19—C65—H65B109.5
C26—C25—C17121.1 (3)H65A—C65—H65B109.5
C25—C26—C27119.9 (3)O19—C65—H65C109.5
C25—C26—H26120.1H65A—C65—H65C109.5
C27—C26—H26120.1H65B—C65—H65C109.5
O8—C27—C28115.8 (3)O20—C66—H66A109.5
O8—C27—C26124.4 (3)O20—C66—H66B109.5
C28—C27—C26119.7 (3)H66A—C66—H66B109.5
C29—C28—O9119.7 (3)O20—C66—H66C109.5
C29—C28—C27120.1 (3)H66A—C66—H66C109.5
O9—C28—C27120.2 (3)H66B—C66—H66C109.5
O10—C29—C28114.9 (3)C67—O21—H21109.5
O10—C29—C30124.9 (3)O21—C67—H67A109.5
C28—C29—C30120.1 (3)O21—C67—H67B109.5
C25—C30—C29120.0 (3)H67A—C67—H67B109.5
C25—C30—H30120.0O21—C67—H67C109.5
C29—C30—H30120.0H67A—C67—H67C109.5
O8—C31—H31A109.5H67B—C67—H67C109.5
O8—C31—H31B109.5C68—O22—H22109.5
H31A—C31—H31B109.5O22—C68—H68A109.5
O8—C31—H31C109.5O22—C68—H68B109.5
H31A—C31—H31C109.5H68A—C68—H68B109.5
H31B—C31—H31C109.5O22—C68—H68C109.5
O9—C32—H32A109.5H68A—C68—H68C109.5
O9—C32—H32B109.5H68B—C68—H68C109.5
H32A—C32—H32B109.5C69—O23—H23A109.5
O9—C32—H32C109.5O23—C69—H69A109.5
H32A—C32—H32C109.5O23—C69—H69B109.5
H32B—C32—H32C109.5H69A—C69—H69B109.5
O10—C33—H33A109.5O23—C69—H69C109.5
O10—C33—H33B109.5H69A—C69—H69C109.5
H33A—C33—H33B109.5H69B—C69—H69C109.5
O10—C33—H33C109.5
C1—O1—C2—C3179.9 (3)C34—O11—C35—C42167.5 (3)
C1—O1—C2—C91.9 (5)C34—O11—C35—C3613.8 (4)
O1—C2—C3—C4176.4 (3)O11—C35—C36—C37179.5 (3)
C9—C2—C3—C41.7 (5)C42—C35—C36—C370.9 (5)
C2—C3—C4—C50.8 (5)C35—C36—C37—C380.7 (5)
C3—C4—C5—N1179.4 (3)C39—N3—C38—C37174.3 (3)
C3—C4—C5—C80.9 (5)C39—N3—C38—C411.1 (3)
C6—N1—C5—C4179.1 (3)C36—C37—C38—N3174.6 (3)
C6—N1—C5—C80.6 (4)C36—C37—C38—C410.2 (5)
C5—N1—C6—C70.4 (4)C38—N3—C39—C400.9 (3)
N1—C6—C7—C10170.1 (3)N3—C39—C40—C43176.5 (3)
N1—C6—C7—C81.2 (4)N3—C39—C40—C410.3 (3)
C4—C5—C8—C91.6 (5)N3—C38—C41—C42177.7 (3)
N1—C5—C8—C9178.7 (3)C37—C38—C41—C421.9 (4)
C4—C5—C8—C7178.4 (3)N3—C38—C41—C400.9 (3)
N1—C5—C8—C71.3 (3)C37—C38—C41—C40174.9 (3)
C6—C7—C8—C51.5 (3)C39—C40—C41—C380.4 (3)
C10—C7—C8—C5170.1 (3)C43—C40—C41—C38176.1 (3)
C6—C7—C8—C9178.4 (3)C39—C40—C41—C42176.6 (3)
C10—C7—C8—C99.9 (5)C43—C40—C41—C420.1 (5)
O1—C2—C9—C8176.9 (3)O11—C35—C42—C41178.3 (2)
C3—C2—C9—C81.0 (5)C36—C35—C42—C413.0 (4)
C5—C8—C9—C20.6 (4)C38—C41—C42—C353.5 (4)
C7—C8—C9—C2179.4 (3)C40—C41—C42—C35172.4 (3)
C6—C7—C10—O2164.5 (3)C39—C40—C43—O12179.9 (3)
C8—C7—C10—O25.2 (5)C41—C40—C43—O124.6 (5)
C6—C7—C10—C1116.9 (5)C39—C40—C43—C440.1 (5)
C8—C7—C10—C11173.3 (3)C41—C40—C43—C44175.7 (3)
C12—N2—C11—O34.4 (5)C45—N4—C44—O134.0 (5)
C12—N2—C11—C10178.7 (3)C45—N4—C44—C43175.8 (2)
O2—C10—C11—O3173.4 (3)O12—C43—C44—O13178.4 (3)
C7—C10—C11—O38.0 (5)C40—C43—C44—O131.9 (4)
O2—C10—C11—N29.7 (4)O12—C43—C44—N41.4 (4)
C7—C10—C11—N2168.9 (3)C40—C43—C44—N4178.4 (3)
C11—N2—C12—C24139.2 (3)C44—N4—C45—C57142.7 (3)
C11—N2—C12—C1397.3 (3)C44—N4—C45—C4696.9 (3)
N2—C12—C13—C1680.5 (3)N4—C45—C46—C4749.4 (4)
C24—C12—C13—C1641.5 (3)C57—C45—C46—C47169.7 (3)
N2—C12—C13—C1437.2 (4)N4—C45—C46—C4967.7 (3)
C24—C12—C13—C14159.1 (3)C57—C45—C46—C4952.6 (3)
C15—O6—C14—C1322.4 (3)C48—O16—C47—C4616.5 (3)
C16—C13—C14—O634.4 (3)C49—C46—C47—O1629.1 (3)
C12—C13—C14—O6156.9 (2)C45—C46—C47—O16149.7 (3)
C14—O6—C15—O7178.7 (3)C47—O16—C48—O17178.7 (3)
C14—O6—C15—C160.3 (3)C47—O16—C48—C493.6 (3)
O7—C15—C16—C13159.0 (3)O17—C48—C49—C46163.3 (3)
O6—C15—C16—C1322.1 (3)O16—C48—C49—C4622.1 (3)
O7—C15—C16—C1733.1 (5)O17—C48—C49—C5035.2 (5)
O6—C15—C16—C17148.0 (3)O16—C48—C49—C50150.2 (3)
C14—C13—C16—C1534.0 (3)C47—C46—C49—C4830.8 (3)
C12—C13—C16—C15162.6 (2)C45—C46—C49—C48158.1 (2)
C14—C13—C16—C17165.1 (2)C47—C46—C49—C50164.0 (2)
C12—C13—C16—C1766.3 (3)C45—C46—C49—C5068.6 (3)
C15—C16—C17—C18176.5 (2)C48—C49—C50—C5843.4 (4)
C13—C16—C17—C1855.1 (3)C46—C49—C50—C5880.4 (3)
C15—C16—C17—C2552.3 (4)C48—C49—C50—C51170.5 (3)
C13—C16—C17—C2569.1 (3)C46—C49—C50—C5146.6 (3)
C25—C17—C18—C1979.5 (3)C58—C50—C51—C57112.6 (3)
C16—C17—C18—C19155.0 (2)C49—C50—C51—C5715.9 (4)
C25—C17—C18—C2499.6 (3)C58—C50—C51—C5267.4 (3)
C16—C17—C18—C2425.9 (4)C49—C50—C51—C52164.1 (3)
C24—C18—C19—C201.3 (4)C57—C51—C52—C530.2 (4)
C17—C18—C19—C20179.5 (3)C50—C51—C52—C53179.7 (3)
C21—O5—C20—C2213.3 (3)C51—C52—C53—O15178.7 (3)
C21—O5—C20—C19167.6 (3)C51—C52—C53—C551.2 (5)
C18—C19—C20—C221.7 (4)C54—O15—C53—C52172.0 (4)
C18—C19—C20—O5179.3 (3)C54—O15—C53—C557.9 (4)
C22—O4—C21—O522.7 (3)C53—O15—C54—O1413.2 (5)
C20—O5—C21—O422.1 (3)C55—O14—C54—O1513.4 (5)
O5—C20—C22—C23179.4 (3)C54—O14—C55—C56170.9 (4)
C19—C20—C22—C230.2 (5)C54—O14—C55—C538.3 (4)
O5—C20—C22—O40.8 (4)C52—C53—C55—C560.9 (5)
C19—C20—C22—O4178.4 (3)O15—C53—C55—C56179.0 (3)
C21—O4—C22—C23166.9 (3)C52—C53—C55—O14179.8 (3)
C21—O4—C22—C2014.6 (3)O15—C53—C55—O140.3 (4)
C20—C22—C23—C241.6 (5)O14—C55—C56—C57178.3 (3)
O4—C22—C23—C24179.9 (3)C53—C55—C56—C570.8 (5)
C22—C23—C24—C181.9 (4)C52—C51—C57—C561.9 (4)
C22—C23—C24—C12173.4 (3)C50—C51—C57—C56178.0 (3)
C19—C18—C24—C230.5 (4)C52—C51—C57—C45174.3 (3)
C17—C18—C24—C23178.7 (3)C50—C51—C57—C455.7 (4)
C19—C18—C24—C12174.5 (3)C55—C56—C57—C512.2 (4)
C17—C18—C24—C126.3 (4)C55—C56—C57—C45174.3 (3)
N2—C12—C24—C2364.3 (3)N4—C45—C57—C5198.9 (3)
C13—C12—C24—C23171.3 (3)C46—C45—C57—C5123.9 (4)
N2—C12—C24—C18110.9 (3)N4—C45—C57—C5677.5 (3)
C13—C12—C24—C1813.5 (4)C46—C45—C57—C56159.7 (3)
C18—C17—C25—C30148.3 (3)C51—C50—C58—C5934.1 (4)
C16—C17—C25—C3090.0 (3)C49—C50—C58—C5990.9 (3)
C18—C17—C25—C2629.8 (4)C51—C50—C58—C63143.9 (3)
C16—C17—C25—C2691.9 (3)C49—C50—C58—C6391.2 (3)
C30—C25—C26—C271.5 (4)C63—C58—C59—C601.6 (4)
C17—C25—C26—C27179.6 (3)C50—C58—C59—C60179.5 (3)
C31—O8—C27—C28175.5 (3)C64—O18—C60—C591.7 (4)
C31—O8—C27—C262.8 (5)C64—O18—C60—C61176.6 (3)
C25—C26—C27—O8178.6 (3)C58—C59—C60—O18178.0 (3)
C25—C26—C27—C280.3 (5)C58—C59—C60—C610.3 (4)
C32—O9—C28—C2993.1 (3)C65—O19—C61—C6275.3 (4)
C32—O9—C28—C2786.4 (4)C65—O19—C61—C60108.7 (4)
O8—C27—C28—C29176.7 (3)O18—C60—C61—O190.1 (4)
C26—C27—C28—C291.7 (5)C59—C60—C61—O19178.6 (3)
O8—C27—C28—O92.7 (4)O18—C60—C61—C62175.9 (2)
C26—C27—C28—O9178.8 (3)C59—C60—C61—C622.5 (4)
C33—O10—C29—C28164.1 (3)C66—O20—C62—C6331.8 (4)
C33—O10—C29—C3014.8 (5)C66—O20—C62—C61149.0 (3)
O9—C28—C29—O103.0 (4)O19—C61—C62—O201.9 (4)
C27—C28—C29—O10176.5 (3)C60—C61—C62—O20177.9 (3)
O9—C28—C29—C30178.1 (3)O19—C61—C62—C63178.8 (3)
C27—C28—C29—C302.5 (5)C60—C61—C62—C632.8 (4)
C26—C25—C30—C290.8 (5)O20—C62—C63—C58180.0 (3)
C17—C25—C30—C29178.9 (3)C61—C62—C63—C580.8 (4)
O10—C29—C30—C25177.6 (3)C59—C58—C63—C621.4 (4)
C28—C29—C30—C251.3 (5)C50—C58—C63—C62179.3 (3)

Experimental details

Crystal data
Chemical formulaC33H30N2O10·CH4O
Mr646.63
Crystal system, space groupMonoclinic, P21
Temperature (K)113
a, b, c (Å)12.228 (2), 9.8360 (16), 26.667 (5)
β (°) 95.58 (3)
V3)3192.2 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.24 × 0.22 × 0.12
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.976, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
22853, 7730, 6754
Rint0.045
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.127, 1.03
No. of reflections7730
No. of parameters893
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.73, 0.27

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the Great Program of Science Foundation of Tianjin (06YFJZJCO2700), the Program of Science Foundation of Tianjin (08JCYBJC070000) and the National Natural Science Foundation of China (No. 30873363).

References

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First citationKnaack, M., Emig, P., Bats, J. W., Kiesel, M., Muller, A. & Gunther, E. (2001). Eur. J. Org. Chem. pp. 3843–3847.  CrossRef Google Scholar
First citationRigaku/MSC (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan, and MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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
First citationZhou, X. M., Wang, Z. Q., Chang, J. Y., Chen, H. X., Cheng, Y. C. & Lee, K. H. (1991). J. Med. Chem. 34, 3346–3350.  CrossRef PubMed CAS Web of Science Google Scholar
First citationZhu, X.-K., Guan, J., Tachibana, Y., Bastow, K. F., Cho, S. J., Cheng, H.-H., Cheng, Y. C., Gurwith, M. & Lee, K.-H. (1999). J. Med. Chem. 42, 2441–2446.  Web of Science CrossRef PubMed CAS Google Scholar

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