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

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ISSN: 2056-9890

1-(2-Hy­dr­oxy­eth­yl)-3-[(2-hy­dr­oxy­eth­yl)amino]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

aCollege of Chemisty, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, People's Republic of China
*Correspondence e-mail: syzhao8@dhu.edu.cn

(Received 25 February 2011; accepted 1 March 2011; online 12 March 2011)

There are four molecules in the asymmetric unit of the title compound, C16H17N3O4, in which the dihedral angles between the indole ring system and maleimide ring are 4.5 (3), 8.3 (3), 8.4 (2) and 10.4 (2)°. In the crystal, mol­ecules are linked by numerous N—H⋯O and O—H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For general background to indolylmaleimides and their biological properties, see: Vegesna et al. (1998)[Vegesna, R. V., Wu, H. L., Mong, S. & Crooke, S. T. (1998). Mol. Pharmacol. 33, 537-542.]; Hu (1996[Hu, H. (1996). Drug Discov. Today, 1, 438-447.]); Zhao et al. (2008[Zhao, S. Y., Shao, Z. Y., Qin, W. M. & Zhang, D. Q. (2008). Chin. J. Org. Chem. 28, 1128-1137.]). For the preparation, see: Zhao et al. (2010[Zhao, S. Y., Jiang, D. F., Yang, Y. W. & Shao, Z. Y. (2010). Lett. Org. Chem. 7, 144-148.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17N3O4

  • Mr = 315.33

  • Triclinic, [P \overline 1]

  • a = 13.0276 (10) Å

  • b = 14.8150 (11) Å

  • c = 17.8893 (14) Å

  • α = 90.012 (1)°

  • β = 110.295 (2)°

  • γ = 102.187 (2)°

  • V = 3155.2 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.43 × 0.33 × 0.27 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.594, Tmax = 1.000

  • 17464 measured reflections

  • 12193 independent reflections

  • 6708 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.098

  • S = 0.89

  • 12193 reflections

  • 893 parameters

  • 13 restraints

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

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O12i 0.86 (3) 2.09 (3) 2.950 (3) 177 (3)
O3—H3⋯O8ii 0.84 (3) 1.93 (3) 2.762 (3) 172 (3)
O4—H4⋯O14iii 0.82 (2) 1.97 (2) 2.770 (2) 163 (3)
N5—H5⋯O16iv 0.83 (2) 2.22 (2) 3.027 (3) 164 (2)
O7—H7⋯O4v 0.86 (2) 1.89 (2) 2.755 (3) 175 (3)
O15—H15⋯O1vi 0.84 (2) 2.22 (2) 2.893 (2) 137 (3)
O15—H15⋯O12vii 0.84 (2) 2.42 (2) 3.097 (3) 139 (3)
O16—H16⋯O11i 0.83 (2) 1.96 (2) 2.780 (3) 170 (3)
N3—H3A⋯O6iii 0.87 (2) 2.06 (2) 2.840 (2) 149 (2)
N6—H6A⋯O14 0.84 (2) 2.22 (2) 3.042 (3) 168 (2)
O8—H8A⋯O10viii 0.85 (2) 1.90 (2) 2.746 (3) 173 (3)
N9—H9A⋯O2viii 0.89 (2) 1.95 (2) 2.760 (2) 152 (2)
O11—H11A⋯O5ii 0.87 (2) 2.13 (2) 2.935 (2) 154 (3)
O11—H11A⋯O16 0.87 (2) 2.51 (3) 3.033 (3) 120 (3)
O12—H12A⋯O15ix 0.84 (2) 1.92 (2) 2.739 (2) 168 (3)
N8—H8B⋯O7x 0.89 (2) 2.09 (2) 2.867 (3) 146 (2)
N11—H11B⋯O3 0.88 (2) 2.17 (2) 2.945 (3) 147 (2)
N12—H12B⋯O10viii 0.85 (2) 2.10 (2) 2.925 (2) 164 (2)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y, z; (iii) x, y, z+1; (iv) x+1, y, z; (v) x+1, y, z-1; (vi) -x, -y+2, -z+1; (vii) x, y+1, z; (viii) -x+1, -y+1, -z+1; (ix) -x, -y+1, -z; (x) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The indolylmaleimides and their derivatives derived from staurosporine, is a specific class of protein kinase C inhibitors,and can be used to treat or prevent a variety of conditions and diseases,such as an inflammatory diseasea or some kinds of cancer disease and so on (Vegesna et al., 1998; Hu, 1996; Zhao et al., 2008). The pharmacological results showed that the title compound displayed potent cytotoxic activity. Our reserach group has focused on the synthesis of the indolylmaleimides and their derivatives and we now report the structure of the title compound, (I).

The X-ray structural analysis confirmed the assignment of its structure from spectroscopic data. The asymmetric unit of (I) contains four independent molecules, each molecules are linked to each other through N—H···O and O—H···O intermolecular hydrogen bonds(Table 1, Fig. 1).The four molecules show slightly different conformations: the dihedral angles between the indole ring and maleimide ring are 4.5 (3), 8.4 (2),10.4 (2) and 8.3 (3)° in the four independent molecules.

In the crystal (Fig. 2),indolylmaleimide molecules are linked by intermolecular N—H···O hydrogen bonds. The layers are further connected into a three-dimensional network by N—H···O and O—H···O hydrogen bonds involving the maleimide molecules as H-donors and by weak ππ stacking interactions involving neighbouring indole and maleimide rings.

Related literature top

For general background to indolylmaleimides and their biological properties, see: Vegesna et al. (1998); Hu (1996); Zhao et al.(2008). For the preparation, see: Zhao et al. (2010).

Experimental top

3-Bromo-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione (0.5 g, 1.67 mmol), 2-aminoethanol(0.15 g, 2.46 mmol) and 1.5 ml triethylamine was added to DMF (8 ml) in a flask. The reaction mixture was stirred at 363 K under argon for 10 h. After the completion of the reaction (determined by TLC), the reaction mixture was cooled to room temperature, and diluted with ethylacetate (80 ml). The solution was washed successively with water (50 ml), brine (50 ml) and then dried with anhydrous magnesium sulfate. The crude material was purified by chromatography with 2:1(hexane-EtOAc) as red crystals (0.31 g, 61%). The crystals were obtained by dissolving the title compound (0.3 g, 1.0 mmol) in ethyl acetate (5 ml) and ethanol (5 ml) and evaporating the solvent slowly at room temperature for about 2 d to yield red blocks.

Refinement top

The H atoms were placed at idealised positions and refined as riding (C—H in the range 0.93 – 0.97 Å) and Uiso(H) (in the range 1.2 - 1.5 Ueq(parent atom)]

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 (I) showing displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Packing of the title compound with hydrogen bonding shown as dashed lines.
1-(2-Hydroxyethyl)-3-[(2-hydroxyethyl)amino]-4-(1H-indol-3-yl)-1H- pyrrole-2,5-dione top
Crystal data top
C16H17N3O4Z = 8
Mr = 315.33F(000) = 1328
Triclinic, P1Dx = 1.328 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.0276 (10) ÅCell parameters from 3141 reflections
b = 14.8150 (11) Åθ = 4.9–45.4°
c = 17.8893 (14) ŵ = 0.10 mm1
α = 90.012 (1)°T = 293 K
β = 110.295 (2)°Prism, red
γ = 102.187 (2)°0.43 × 0.33 × 0.27 mm
V = 3155.2 (4) Å3
Data collection top
Bruker SMART CCD
diffractometer
12193 independent reflections
Radiation source: fine-focus sealed tube6708 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 168
Tmin = 0.594, Tmax = 1.000k = 1818
17464 measured reflectionsl = 2222
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 0.89 w = 1/[σ2(Fo2) + (0.0246P)2]
where P = (Fo2 + 2Fc2)/3
12193 reflections(Δ/σ)max = 0.002
893 parametersΔρmax = 0.18 e Å3
13 restraintsΔρmin = 0.18 e Å3
Crystal data top
C16H17N3O4γ = 102.187 (2)°
Mr = 315.33V = 3155.2 (4) Å3
Triclinic, P1Z = 8
a = 13.0276 (10) ÅMo Kα radiation
b = 14.8150 (11) ŵ = 0.10 mm1
c = 17.8893 (14) ÅT = 293 K
α = 90.012 (1)°0.43 × 0.33 × 0.27 mm
β = 110.295 (2)°
Data collection top
Bruker SMART CCD
diffractometer
12193 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
6708 reflections with I > 2σ(I)
Tmin = 0.594, Tmax = 1.000Rint = 0.035
17464 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04713 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 0.89Δρmax = 0.18 e Å3
12193 reflectionsΔρmin = 0.18 e Å3
893 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.01888 (14)0.90744 (12)0.80210 (9)0.0565 (5)
O20.29635 (13)0.85115 (12)0.72416 (9)0.0504 (5)
O30.04854 (17)0.83153 (15)0.57712 (11)0.0565 (6)
O40.15970 (17)0.77882 (16)1.08999 (12)0.0692 (6)
O50.95648 (14)0.59360 (11)0.28315 (9)0.0535 (5)
O60.67689 (14)0.66239 (12)0.07237 (9)0.0513 (5)
O70.94607 (17)0.67135 (14)0.05474 (11)0.0538 (5)
O80.84197 (16)0.71019 (15)0.51014 (12)0.0638 (6)
O90.07500 (14)0.42150 (11)0.14849 (9)0.0545 (5)
O100.27077 (13)0.32299 (11)0.38483 (9)0.0452 (4)
O110.03045 (15)0.43298 (14)0.37925 (10)0.0511 (5)
O120.03693 (16)0.11914 (13)0.04475 (11)0.0539 (5)
O130.07026 (14)0.90731 (11)0.37576 (10)0.0518 (5)
O140.28453 (13)0.81144 (11)0.25196 (9)0.0451 (4)
O150.03425 (16)0.92783 (14)0.10409 (10)0.0547 (5)
O160.03196 (16)0.62001 (13)0.47197 (11)0.0551 (5)
N10.14842 (15)0.89266 (13)0.74548 (10)0.0372 (5)
N20.11889 (18)0.78733 (15)0.91611 (12)0.0465 (6)
N30.47775 (18)0.70845 (14)0.96808 (12)0.0434 (6)
N40.82676 (16)0.61586 (13)0.16343 (11)0.0388 (5)
N50.86558 (18)0.71354 (15)0.35412 (12)0.0455 (6)
N60.50460 (18)0.79428 (15)0.23571 (13)0.0466 (6)
N70.15305 (15)0.37924 (13)0.27663 (11)0.0392 (5)
N80.19072 (18)0.29920 (14)0.10367 (12)0.0425 (5)
N90.50170 (18)0.18774 (15)0.26645 (13)0.0460 (6)
N100.15776 (15)0.86570 (13)0.29283 (11)0.0385 (5)
N110.19009 (17)0.79605 (14)0.48792 (12)0.0422 (5)
N120.51134 (18)0.68804 (15)0.49777 (13)0.0451 (6)
C10.0978 (2)0.87718 (16)0.80078 (13)0.0370 (6)
C20.15798 (19)0.81481 (15)0.85866 (13)0.0333 (6)
C30.24264 (18)0.79819 (15)0.83623 (13)0.0330 (6)
C40.23771 (19)0.84653 (16)0.76469 (14)0.0371 (6)
C50.33199 (18)0.74941 (15)0.87521 (13)0.0325 (6)
C60.41135 (19)0.77124 (16)0.95001 (13)0.0396 (6)
H60.41910.82180.98390.048*
C70.44387 (19)0.64506 (16)0.90381 (14)0.0370 (6)
C80.35307 (18)0.66880 (15)0.84379 (13)0.0313 (5)
C90.30427 (19)0.61489 (16)0.77103 (14)0.0411 (6)
H90.24430.62910.73000.049*
C100.3471 (2)0.54000 (16)0.76140 (16)0.0496 (7)
H100.31610.50390.71300.060*
C110.4362 (2)0.51745 (17)0.82295 (17)0.0538 (7)
H110.46230.46580.81490.065*
C120.4857 (2)0.56879 (17)0.89430 (15)0.0470 (7)
H120.54520.55350.93500.056*
C130.1222 (2)0.95368 (16)0.68137 (13)0.0449 (7)
H13A0.18710.97340.66560.054*
H13B0.10661.00850.70090.054*
C140.0232 (2)0.90832 (18)0.60956 (14)0.0564 (8)
H14A0.04200.88730.62480.068*
H14B0.00600.95260.56970.068*
C150.1534 (2)0.71408 (16)0.96736 (13)0.0446 (7)
H15A0.19380.68110.94450.054*
H15B0.08670.67030.96770.054*
C160.2259 (2)0.7482 (2)1.05170 (14)0.0603 (8)
H16A0.25760.69881.07960.072*
H16B0.28720.79891.05240.072*
C170.8788 (2)0.62661 (16)0.24387 (14)0.0383 (6)
C180.82312 (19)0.68873 (15)0.27522 (13)0.0338 (6)
C190.73717 (18)0.70832 (15)0.21321 (13)0.0327 (6)
C200.73834 (19)0.66356 (16)0.14114 (14)0.0376 (6)
C210.64887 (18)0.75675 (15)0.21160 (13)0.0340 (6)
C220.57272 (19)0.73278 (16)0.24882 (13)0.0411 (6)
H220.56790.68190.27880.049*
C230.5339 (2)0.85913 (16)0.18788 (14)0.0399 (6)
C240.62425 (19)0.83761 (16)0.17098 (13)0.0353 (6)
C250.6702 (2)0.89384 (16)0.12269 (14)0.0448 (7)
H250.73000.88120.11080.054*
C260.6254 (2)0.96828 (17)0.09301 (15)0.0578 (8)
H260.65451.00570.06000.069*
C270.5366 (3)0.98819 (18)0.11196 (17)0.0637 (9)
H270.50881.03950.09180.076*
C280.4897 (2)0.93519 (18)0.15875 (15)0.0539 (8)
H280.43060.94910.17080.065*
C290.8468 (2)0.55311 (17)0.11019 (14)0.0490 (7)
H29A0.78460.54260.05950.059*
H29B0.84950.49400.13320.059*
C300.9545 (2)0.58963 (18)0.09541 (15)0.0553 (8)
H30A1.01710.60310.14590.066*
H30B0.96760.54350.06340.066*
C310.83718 (19)0.78606 (16)0.39233 (13)0.0440 (7)
H31A0.79320.81960.35140.053*
H31B0.90580.82940.42430.053*
C320.7726 (2)0.75013 (19)0.44452 (15)0.0561 (8)
H32A0.74900.80030.46420.067*
H32B0.70600.70380.41410.067*
C330.13398 (19)0.37915 (16)0.19553 (14)0.0392 (6)
C340.20150 (18)0.31586 (15)0.17965 (13)0.0335 (6)
C350.26342 (18)0.28810 (15)0.25086 (12)0.0310 (5)
C360.23384 (18)0.32799 (16)0.31208 (14)0.0356 (6)
C370.35094 (18)0.23509 (15)0.26947 (13)0.0321 (6)
C380.43740 (19)0.25097 (16)0.24109 (13)0.0395 (6)
H380.45050.29820.20900.047*
C390.4593 (2)0.13065 (16)0.31364 (14)0.0396 (6)
C400.36477 (18)0.15878 (15)0.31827 (12)0.0317 (6)
C410.3088 (2)0.11198 (16)0.36590 (13)0.0415 (6)
H410.24590.12880.36990.050*
C420.3489 (2)0.04011 (17)0.40695 (14)0.0536 (7)
H420.31400.00960.44020.064*
C430.4413 (2)0.01276 (18)0.39907 (16)0.0573 (8)
H430.46520.03680.42620.069*
C440.4973 (2)0.05634 (18)0.35303 (15)0.0521 (7)
H440.55840.03740.34800.062*
C450.11261 (18)0.43681 (16)0.32088 (14)0.0424 (6)
H45A0.10770.49500.29650.051*
H45B0.16550.45050.37540.051*
C460.00130 (19)0.38894 (16)0.32173 (14)0.0451 (7)
H46A0.05740.38880.26920.054*
H46B0.00110.32500.33340.054*
C470.2206 (2)0.22208 (17)0.07274 (14)0.0439 (7)
H47A0.30020.22540.09960.053*
H47B0.20670.22680.01610.053*
C480.1548 (2)0.13003 (17)0.08450 (14)0.0489 (7)
H48A0.17910.08070.06440.059*
H48B0.17050.12460.14120.059*
C490.1340 (2)0.86713 (16)0.36197 (14)0.0383 (6)
C500.20470 (18)0.80888 (15)0.41787 (13)0.0332 (6)
C510.27068 (18)0.78090 (15)0.38135 (13)0.0313 (6)
C520.24286 (19)0.81751 (15)0.30282 (13)0.0354 (6)
C530.36095 (18)0.73141 (15)0.41251 (13)0.0314 (5)
C540.44338 (19)0.74950 (16)0.48690 (13)0.0399 (6)
H540.45180.79660.52440.048*
C550.47595 (19)0.62988 (16)0.42986 (14)0.0382 (6)
C560.38155 (18)0.65533 (15)0.37388 (13)0.0336 (6)
C570.3320 (2)0.60708 (16)0.29817 (14)0.0419 (6)
H570.27070.62310.25980.050*
C580.3747 (2)0.53610 (17)0.28139 (16)0.0519 (7)
H580.34230.50430.23100.062*
C590.4657 (2)0.51040 (17)0.33818 (19)0.0589 (8)
H590.49200.46110.32520.071*
C600.5177 (2)0.55631 (17)0.41323 (17)0.0526 (7)
H600.57820.53880.45120.063*
C610.11773 (19)0.92236 (16)0.22703 (13)0.0419 (6)
H61A0.16540.92800.19520.050*
H61B0.12290.98400.24840.050*
C620.00267 (19)0.88101 (16)0.17422 (13)0.0458 (7)
H62A0.01070.81610.16000.055*
H62B0.05210.88510.20340.055*
C630.2175 (2)0.71998 (17)0.53710 (13)0.0447 (7)
H63A0.20260.72760.58600.054*
H63B0.29680.72140.55160.054*
C640.1493 (2)0.62799 (17)0.49328 (14)0.0490 (7)
H64A0.16600.62000.44520.059*
H64B0.17120.57880.52680.059*
H20.076 (2)0.8158 (18)0.9294 (16)0.090 (11)*
H30.011 (3)0.790 (2)0.5591 (19)0.110 (15)*
H40.197 (2)0.800 (2)1.1362 (12)0.115 (14)*
H50.9167 (16)0.6879 (14)0.3791 (12)0.049 (8)*
H71.0115 (17)0.7078 (19)0.0656 (18)0.108 (14)*
H150.028 (2)0.9853 (12)0.1074 (17)0.091 (12)*
H160.023 (2)0.602 (2)0.5139 (13)0.101 (13)*
H3A0.5346 (18)0.7095 (15)1.0115 (13)0.052 (8)*
H6A0.4477 (16)0.7952 (16)0.2469 (14)0.058 (9)*
H8A0.811 (3)0.698 (2)0.5447 (16)0.135 (16)*
H9A0.5621 (17)0.1857 (18)0.2545 (15)0.080 (10)*
H11A0.033 (3)0.4887 (15)0.366 (2)0.154 (17)*
H12A0.027 (2)0.107 (2)0.0032 (11)0.093 (12)*
H8B0.1419 (16)0.3246 (14)0.0672 (11)0.048 (7)*
H11B0.1432 (18)0.8233 (16)0.4995 (14)0.069 (9)*
H12B0.5704 (15)0.6903 (15)0.5382 (11)0.049 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0597 (13)0.0772 (14)0.0560 (12)0.0461 (11)0.0314 (10)0.0174 (10)
O20.0435 (11)0.0797 (13)0.0431 (11)0.0321 (10)0.0236 (9)0.0174 (9)
O30.0509 (14)0.0726 (15)0.0496 (12)0.0228 (12)0.0170 (11)0.0068 (11)
O40.0552 (14)0.1098 (18)0.0406 (13)0.0169 (13)0.0156 (11)0.0074 (12)
O50.0549 (12)0.0731 (13)0.0429 (11)0.0418 (11)0.0143 (9)0.0183 (9)
O60.0514 (11)0.0722 (13)0.0305 (10)0.0289 (10)0.0060 (9)0.0096 (9)
O70.0554 (14)0.0656 (14)0.0470 (12)0.0218 (12)0.0214 (10)0.0197 (10)
O80.0537 (13)0.0957 (16)0.0469 (13)0.0176 (11)0.0235 (11)0.0183 (11)
O90.0572 (12)0.0552 (12)0.0468 (11)0.0332 (10)0.0013 (9)0.0096 (9)
O100.0417 (10)0.0694 (12)0.0323 (10)0.0268 (9)0.0144 (8)0.0087 (9)
O110.0595 (13)0.0595 (13)0.0523 (12)0.0251 (11)0.0351 (10)0.0145 (10)
O120.0525 (13)0.0704 (14)0.0423 (12)0.0164 (10)0.0197 (10)0.0045 (10)
O130.0498 (12)0.0578 (12)0.0648 (12)0.0289 (10)0.0317 (10)0.0136 (9)
O140.0454 (11)0.0672 (12)0.0324 (10)0.0247 (9)0.0188 (9)0.0079 (9)
O150.0686 (13)0.0596 (14)0.0331 (11)0.0310 (12)0.0048 (9)0.0052 (10)
O160.0522 (13)0.0697 (14)0.0436 (12)0.0154 (10)0.0162 (10)0.0154 (11)
N10.0381 (12)0.0498 (13)0.0312 (11)0.0256 (10)0.0121 (10)0.0097 (10)
N20.0517 (15)0.0619 (16)0.0417 (13)0.0298 (13)0.0263 (12)0.0115 (11)
N30.0378 (14)0.0549 (15)0.0330 (13)0.0196 (12)0.0018 (11)0.0042 (11)
N40.0421 (13)0.0528 (13)0.0291 (12)0.0239 (11)0.0143 (10)0.0096 (10)
N50.0465 (15)0.0574 (15)0.0371 (14)0.0279 (13)0.0110 (11)0.0079 (11)
N60.0369 (14)0.0566 (15)0.0551 (15)0.0204 (12)0.0214 (12)0.0087 (12)
N70.0344 (12)0.0513 (13)0.0364 (12)0.0251 (11)0.0092 (10)0.0041 (10)
N80.0536 (15)0.0486 (14)0.0276 (12)0.0234 (12)0.0103 (11)0.0120 (10)
N90.0385 (14)0.0625 (16)0.0504 (14)0.0248 (12)0.0244 (12)0.0141 (12)
N100.0371 (12)0.0494 (13)0.0363 (12)0.0216 (10)0.0152 (10)0.0124 (10)
N110.0489 (14)0.0488 (14)0.0419 (13)0.0211 (12)0.0261 (11)0.0068 (11)
N120.0337 (14)0.0584 (15)0.0400 (14)0.0212 (12)0.0029 (11)0.0089 (12)
C10.0368 (15)0.0461 (16)0.0333 (14)0.0188 (13)0.0135 (12)0.0013 (12)
C20.0347 (14)0.0404 (15)0.0267 (13)0.0142 (12)0.0102 (11)0.0013 (11)
C30.0296 (14)0.0403 (15)0.0292 (13)0.0129 (11)0.0076 (11)0.0005 (11)
C40.0318 (15)0.0488 (16)0.0336 (14)0.0169 (12)0.0104 (12)0.0023 (12)
C50.0294 (14)0.0396 (14)0.0309 (14)0.0120 (11)0.0114 (11)0.0038 (11)
C60.0389 (15)0.0461 (16)0.0373 (15)0.0199 (13)0.0117 (12)0.0010 (12)
C70.0350 (15)0.0424 (15)0.0392 (15)0.0156 (12)0.0160 (12)0.0084 (12)
C80.0268 (13)0.0351 (14)0.0345 (14)0.0072 (11)0.0140 (11)0.0043 (11)
C90.0313 (14)0.0473 (16)0.0436 (16)0.0068 (13)0.0130 (12)0.0011 (13)
C100.0510 (18)0.0426 (17)0.0570 (18)0.0001 (14)0.0274 (15)0.0108 (14)
C110.0557 (19)0.0393 (16)0.080 (2)0.0192 (15)0.0355 (17)0.0076 (15)
C120.0482 (17)0.0472 (17)0.0523 (17)0.0202 (14)0.0206 (14)0.0131 (14)
C130.0509 (17)0.0503 (17)0.0401 (15)0.0235 (14)0.0172 (13)0.0099 (13)
C140.061 (2)0.078 (2)0.0418 (16)0.0408 (17)0.0166 (15)0.0090 (15)
C150.0472 (16)0.0549 (17)0.0383 (15)0.0188 (14)0.0189 (13)0.0102 (13)
C160.0465 (18)0.089 (2)0.0452 (18)0.0192 (16)0.0143 (15)0.0030 (16)
C170.0362 (15)0.0462 (16)0.0384 (15)0.0153 (13)0.0171 (12)0.0137 (12)
C180.0337 (14)0.0393 (15)0.0313 (14)0.0098 (12)0.0142 (12)0.0084 (11)
C190.0303 (14)0.0379 (14)0.0332 (14)0.0133 (11)0.0121 (11)0.0105 (11)
C200.0364 (15)0.0450 (16)0.0352 (15)0.0153 (13)0.0137 (12)0.0126 (12)
C210.0310 (14)0.0376 (15)0.0333 (14)0.0112 (12)0.0094 (11)0.0080 (11)
C220.0371 (15)0.0434 (16)0.0455 (16)0.0157 (13)0.0140 (13)0.0140 (12)
C230.0365 (15)0.0380 (15)0.0409 (15)0.0122 (13)0.0062 (12)0.0055 (12)
C240.0292 (14)0.0386 (15)0.0330 (14)0.0078 (12)0.0046 (11)0.0039 (11)
C250.0430 (16)0.0444 (16)0.0381 (15)0.0013 (13)0.0086 (13)0.0057 (13)
C260.067 (2)0.0431 (18)0.0493 (18)0.0033 (16)0.0085 (16)0.0145 (14)
C270.072 (2)0.0398 (18)0.062 (2)0.0194 (17)0.0010 (17)0.0062 (15)
C280.0518 (18)0.0496 (18)0.0556 (19)0.0239 (15)0.0059 (15)0.0022 (15)
C290.0619 (19)0.0483 (17)0.0476 (16)0.0227 (15)0.0269 (15)0.0106 (13)
C300.066 (2)0.070 (2)0.0490 (17)0.0431 (17)0.0280 (15)0.0202 (15)
C310.0412 (16)0.0554 (17)0.0350 (15)0.0133 (14)0.0118 (12)0.0014 (13)
C320.0429 (17)0.080 (2)0.0473 (18)0.0161 (16)0.0178 (14)0.0060 (16)
C330.0344 (15)0.0390 (15)0.0377 (15)0.0081 (12)0.0049 (12)0.0013 (12)
C340.0342 (14)0.0360 (14)0.0313 (14)0.0108 (12)0.0111 (11)0.0060 (11)
C350.0289 (14)0.0366 (14)0.0305 (13)0.0112 (11)0.0121 (11)0.0058 (11)
C360.0267 (14)0.0463 (16)0.0330 (15)0.0107 (12)0.0083 (12)0.0070 (12)
C370.0285 (14)0.0400 (15)0.0310 (13)0.0138 (11)0.0107 (11)0.0058 (11)
C380.0371 (15)0.0502 (16)0.0395 (15)0.0203 (13)0.0179 (12)0.0174 (12)
C390.0364 (15)0.0448 (16)0.0360 (15)0.0171 (13)0.0064 (12)0.0021 (12)
C400.0273 (14)0.0362 (14)0.0284 (13)0.0067 (11)0.0063 (11)0.0007 (11)
C410.0389 (15)0.0431 (16)0.0373 (15)0.0034 (13)0.0105 (12)0.0032 (12)
C420.063 (2)0.0462 (17)0.0385 (16)0.0031 (15)0.0109 (14)0.0114 (13)
C430.068 (2)0.0400 (17)0.0516 (19)0.0206 (16)0.0008 (16)0.0070 (14)
C440.0538 (18)0.0551 (19)0.0487 (18)0.0284 (15)0.0104 (15)0.0039 (15)
C450.0318 (15)0.0484 (16)0.0490 (16)0.0172 (13)0.0121 (12)0.0018 (13)
C460.0417 (16)0.0485 (17)0.0480 (16)0.0142 (13)0.0172 (13)0.0031 (13)
C470.0443 (16)0.0616 (18)0.0315 (14)0.0211 (14)0.0150 (12)0.0036 (13)
C480.0599 (19)0.0575 (18)0.0363 (15)0.0292 (16)0.0164 (14)0.0038 (13)
C490.0338 (15)0.0360 (15)0.0478 (16)0.0100 (12)0.0165 (13)0.0035 (12)
C500.0335 (14)0.0332 (14)0.0332 (14)0.0078 (11)0.0121 (12)0.0004 (11)
C510.0291 (13)0.0354 (14)0.0292 (13)0.0095 (11)0.0086 (11)0.0003 (11)
C520.0314 (14)0.0402 (15)0.0341 (15)0.0122 (12)0.0084 (12)0.0019 (12)
C530.0304 (14)0.0352 (14)0.0305 (13)0.0116 (11)0.0107 (11)0.0038 (11)
C540.0364 (15)0.0463 (16)0.0380 (15)0.0150 (13)0.0112 (12)0.0022 (12)
C550.0371 (15)0.0404 (15)0.0441 (16)0.0129 (13)0.0206 (13)0.0069 (12)
C560.0293 (14)0.0370 (14)0.0384 (14)0.0081 (11)0.0166 (12)0.0052 (12)
C570.0404 (16)0.0433 (16)0.0431 (16)0.0045 (13)0.0191 (13)0.0031 (13)
C580.0554 (19)0.0402 (16)0.0628 (19)0.0009 (14)0.0311 (16)0.0113 (14)
C590.071 (2)0.0365 (17)0.092 (2)0.0117 (16)0.0566 (19)0.0039 (16)
C600.0516 (18)0.0491 (18)0.075 (2)0.0267 (15)0.0353 (16)0.0211 (15)
C610.0410 (16)0.0461 (16)0.0416 (15)0.0183 (13)0.0136 (13)0.0130 (12)
C620.0467 (17)0.0471 (17)0.0418 (16)0.0155 (14)0.0109 (13)0.0019 (13)
C630.0451 (16)0.0630 (19)0.0337 (15)0.0216 (14)0.0180 (13)0.0122 (13)
C640.0591 (19)0.0501 (18)0.0486 (17)0.0232 (15)0.0261 (15)0.0142 (14)
Geometric parameters (Å, º) top
O1—C11.212 (2)C15—H15B0.9700
O2—C41.215 (3)C16—H16A0.9700
O3—C141.426 (3)C16—H16B0.9700
O3—H30.84 (3)C17—C181.500 (3)
O4—C161.412 (3)C18—C191.358 (3)
O4—H40.822 (17)C19—C201.456 (3)
O5—C171.214 (2)C19—C211.471 (3)
O6—C201.211 (2)C21—C221.365 (3)
O7—C301.417 (3)C21—C241.438 (3)
O7—H70.864 (17)C22—H220.9300
O8—C321.427 (3)C23—C281.392 (3)
O8—H8A0.846 (18)C23—C241.409 (3)
O9—C331.203 (2)C24—C251.395 (3)
O10—C361.229 (2)C25—C261.377 (3)
O11—C461.416 (3)C25—H250.9300
O11—H11A0.866 (18)C26—C271.399 (3)
O12—C481.423 (3)C26—H260.9300
O12—H12A0.836 (16)C27—C281.358 (4)
O13—C491.207 (2)C27—H270.9300
O14—C521.222 (2)C28—H280.9300
O15—C621.410 (3)C29—C301.506 (3)
O15—H150.838 (16)C29—H29A0.9700
O16—C641.420 (3)C29—H29B0.9700
O16—H160.831 (17)C30—H30A0.9700
N1—C11.362 (3)C30—H30B0.9700
N1—C41.413 (2)C31—C321.490 (3)
N1—C131.452 (3)C31—H31A0.9700
N2—C21.326 (3)C31—H31B0.9700
N2—C151.463 (3)C32—H32A0.9700
N2—H20.86 (3)C32—H32B0.9700
N3—C61.365 (3)C33—C341.502 (3)
N3—C71.368 (3)C34—C351.368 (3)
N3—H3A0.87 (2)C35—C361.444 (3)
N4—C171.354 (3)C35—C371.464 (3)
N4—C201.418 (3)C37—C381.366 (3)
N4—C291.454 (3)C37—C401.432 (3)
N5—C181.344 (3)C38—H380.9300
N5—C311.450 (3)C39—C441.393 (3)
N5—H50.829 (15)C39—C401.409 (3)
N6—C221.367 (3)C40—C411.399 (3)
N6—C231.368 (3)C41—C421.384 (3)
N6—H6A0.835 (15)C41—H410.9300
N7—C331.384 (3)C42—C431.399 (3)
N7—C361.400 (2)C42—H420.9300
N7—C451.453 (2)C43—C441.358 (4)
N8—C341.334 (3)C43—H430.9300
N8—C471.449 (3)C44—H440.9300
N8—H8B0.886 (15)C45—C461.509 (3)
N9—C381.361 (3)C45—H45A0.9700
N9—C391.364 (3)C45—H45B0.9700
N9—H9A0.890 (16)C46—H46A0.9700
N10—C491.376 (3)C46—H46B0.9700
N10—C521.403 (2)C47—C481.507 (3)
N10—C611.457 (3)C47—H47A0.9700
N11—C501.339 (3)C47—H47B0.9700
N11—C631.457 (3)C48—H48A0.9700
N11—H11B0.878 (15)C48—H48B0.9700
N12—C541.368 (3)C49—C501.513 (3)
N12—C551.369 (3)C50—C511.370 (3)
N12—H12B0.848 (15)C51—C521.459 (3)
C1—C21.511 (3)C51—C531.463 (3)
C2—C31.364 (3)C53—C541.372 (3)
C3—C41.455 (3)C53—C561.441 (3)
C3—C51.468 (3)C54—H540.9300
C5—C61.365 (3)C55—C601.391 (3)
C5—C81.436 (3)C55—C561.414 (3)
C6—H60.9300C56—C571.400 (3)
C7—C121.388 (3)C57—C581.367 (3)
C7—C81.404 (3)C57—H570.9300
C8—C91.396 (3)C58—C591.392 (3)
C9—C101.378 (3)C58—H580.9300
C9—H90.9300C59—C601.378 (3)
C10—C111.395 (3)C59—H590.9300
C10—H100.9300C60—H600.9300
C11—C121.358 (3)C61—C621.515 (3)
C11—H110.9300C61—H61A0.9700
C12—H120.9300C61—H61B0.9700
C13—C141.500 (3)C62—H62A0.9700
C13—H13A0.9700C62—H62B0.9700
C13—H13B0.9700C63—C641.505 (3)
C14—H14A0.9700C63—H63A0.9700
C14—H14B0.9700C63—H63B0.9700
C15—C161.495 (3)C64—H64A0.9700
C15—H15A0.9700C64—H64B0.9700
C14—O3—H3108 (2)C30—C29—H29A109.0
C16—O4—H4111 (2)N4—C29—H29B109.0
C30—O7—H7111 (2)C30—C29—H29B109.0
C32—O8—H8A111 (2)H29A—C29—H29B107.8
C46—O11—H11A107 (2)O7—C30—C29108.9 (2)
C48—O12—H12A104 (2)O7—C30—H30A109.9
C62—O15—H15120 (2)C29—C30—H30A109.9
C64—O16—H16100 (2)O7—C30—H30B109.9
C1—N1—C4109.12 (19)C29—C30—H30B109.9
C1—N1—C13125.62 (19)H30A—C30—H30B108.3
C4—N1—C13125.0 (2)N5—C31—C32113.1 (2)
C2—N2—C15123.8 (2)N5—C31—H31A109.0
C2—N2—H2121.5 (19)C32—C31—H31A109.0
C15—N2—H2114.3 (19)N5—C31—H31B109.0
C6—N3—C7108.72 (19)C32—C31—H31B109.0
C6—N3—H3A126.6 (15)H31A—C31—H31B107.8
C7—N3—H3A124.6 (15)O8—C32—C31109.1 (2)
C17—N4—C20109.35 (18)O8—C32—H32A109.9
C17—N4—C29124.79 (19)C31—C32—H32A109.9
C20—N4—C29125.17 (19)O8—C32—H32B109.9
C18—N5—C31124.7 (2)C31—C32—H32B109.9
C18—N5—H5113.3 (16)H32A—C32—H32B108.3
C31—N5—H5121.6 (16)O9—C33—N7126.2 (2)
C22—N6—C23109.1 (2)O9—C33—C34128.0 (2)
C22—N6—H6A132.4 (18)N7—C33—C34105.74 (19)
C23—N6—H6A118.1 (17)N8—C34—C35134.2 (2)
C33—N7—C36109.16 (18)N8—C34—C33117.10 (19)
C33—N7—C45125.60 (18)C35—C34—C33108.75 (19)
C36—N7—C45124.32 (19)C34—C35—C36106.81 (19)
C34—N8—C47125.5 (2)C34—C35—C37130.6 (2)
C34—N8—H8B116.7 (14)C36—C35—C37122.42 (19)
C47—N8—H8B114.6 (14)O10—C36—N7121.5 (2)
C38—N9—C39108.7 (2)O10—C36—C35129.2 (2)
C38—N9—H9A124.7 (18)N7—C36—C35109.28 (19)
C39—N9—H9A126.6 (18)C38—C37—C40106.50 (19)
C49—N10—C52109.52 (19)C38—C37—C35124.5 (2)
C49—N10—C61124.06 (19)C40—C37—C35129.0 (2)
C52—N10—C61125.21 (19)N9—C38—C37110.3 (2)
C50—N11—C63125.1 (2)N9—C38—H38124.9
C50—N11—H11B118.9 (16)C37—C38—H38124.9
C63—N11—H11B113.3 (17)N9—C39—C44129.3 (2)
C54—N12—C55109.22 (19)N9—C39—C40108.3 (2)
C54—N12—H12B124.6 (15)C44—C39—C40122.4 (3)
C55—N12—H12B125.8 (15)C41—C40—C39118.8 (2)
O1—C1—N1126.0 (2)C41—C40—C37135.0 (2)
O1—C1—C2127.2 (2)C39—C40—C37106.2 (2)
N1—C1—C2106.81 (19)C42—C41—C40118.6 (2)
N2—C2—C3134.6 (2)C42—C41—H41120.7
N2—C2—C1117.1 (2)C40—C41—H41120.7
C3—C2—C1108.3 (2)C41—C42—C43120.8 (3)
C2—C3—C4106.90 (19)C41—C42—H42119.6
C2—C3—C5130.7 (2)C43—C42—H42119.6
C4—C3—C5122.2 (2)C44—C43—C42122.1 (2)
O2—C4—N1121.1 (2)C44—C43—H43118.9
O2—C4—C3130.0 (2)C42—C43—H43118.9
N1—C4—C3108.9 (2)C43—C44—C39117.2 (3)
C6—C5—C8105.93 (19)C43—C44—H44121.4
C6—C5—C3126.5 (2)C39—C44—H44121.4
C8—C5—C3127.6 (2)N7—C45—C46111.06 (19)
C5—C6—N3110.5 (2)N7—C45—H45A109.4
C5—C6—H6124.7C46—C45—H45A109.4
N3—C6—H6124.7N7—C45—H45B109.4
N3—C7—C12129.6 (2)C46—C45—H45B109.4
N3—C7—C8107.84 (19)H45A—C45—H45B108.0
C12—C7—C8122.6 (2)O11—C46—C45111.87 (19)
C9—C8—C7118.9 (2)O11—C46—H46A109.2
C9—C8—C5134.2 (2)C45—C46—H46A109.2
C7—C8—C5106.97 (19)O11—C46—H46B109.2
C10—C9—C8118.4 (2)C45—C46—H46B109.2
C10—C9—H9120.8H46A—C46—H46B107.9
C8—C9—H9120.8N8—C47—C48112.0 (2)
C9—C10—C11121.2 (2)N8—C47—H47A109.2
C9—C10—H10119.4C48—C47—H47A109.2
C11—C10—H10119.4N8—C47—H47B109.2
C12—C11—C10121.8 (2)C48—C47—H47B109.2
C12—C11—H11119.1H47A—C47—H47B107.9
C10—C11—H11119.1O12—C48—C47112.37 (19)
C11—C12—C7117.2 (2)O12—C48—H48A109.1
C11—C12—H12121.4C47—C48—H48A109.1
C7—C12—H12121.4O12—C48—H48B109.1
N1—C13—C14112.7 (2)C47—C48—H48B109.1
N1—C13—H13A109.1H48A—C48—H48B107.9
C14—C13—H13A109.1O13—C49—N10127.0 (2)
N1—C13—H13B109.1O13—C49—C50126.6 (2)
C14—C13—H13B109.1N10—C49—C50106.34 (19)
H13A—C13—H13B107.8N11—C50—C51135.2 (2)
O3—C14—C13109.3 (2)N11—C50—C49116.7 (2)
O3—C14—H14A109.8C51—C50—C49108.1 (2)
C13—C14—H14A109.8C50—C51—C52107.10 (19)
O3—C14—H14B109.8C50—C51—C53129.9 (2)
C13—C14—H14B109.8C52—C51—C53122.75 (19)
H14A—C14—H14B108.3O14—C52—N10122.5 (2)
N2—C15—C16114.1 (2)O14—C52—C51128.7 (2)
N2—C15—H15A108.7N10—C52—C51108.79 (19)
C16—C15—H15A108.7C54—C53—C56106.44 (19)
N2—C15—H15B108.7C54—C53—C51125.21 (19)
C16—C15—H15B108.7C56—C53—C51128.4 (2)
H15A—C15—H15B107.6N12—C54—C53110.0 (2)
O4—C16—C15108.7 (2)N12—C54—H54125.0
O4—C16—H16A110.0C53—C54—H54125.0
C15—C16—H16A110.0N12—C55—C60130.0 (2)
O4—C16—H16B110.0N12—C55—C56107.84 (19)
C15—C16—H16B110.0C60—C55—C56122.1 (2)
H16A—C16—H16B108.3C57—C56—C55118.5 (2)
O5—C17—N4126.8 (2)C57—C56—C53135.0 (2)
O5—C17—C18126.4 (2)C55—C56—C53106.50 (19)
N4—C17—C18106.73 (19)C58—C57—C56119.2 (2)
N5—C18—C19133.9 (2)C58—C57—H57120.4
N5—C18—C17117.3 (2)C56—C57—H57120.4
C19—C18—C17108.8 (2)C57—C58—C59121.4 (2)
C18—C19—C20106.70 (19)C57—C58—H58119.3
C18—C19—C21131.2 (2)C59—C58—H58119.3
C20—C19—C21121.95 (19)C60—C59—C58121.5 (2)
O6—C20—N4122.2 (2)C60—C59—H59119.3
O6—C20—C19129.5 (2)C58—C59—H59119.3
N4—C20—C19108.30 (19)C59—C60—C55117.3 (2)
C22—C21—C24106.0 (2)C59—C60—H60121.4
C22—C21—C19126.2 (2)C55—C60—H60121.4
C24—C21—C19127.8 (2)N10—C61—C62111.7 (2)
C21—C22—N6110.4 (2)N10—C61—H61A109.3
C21—C22—H22124.8C62—C61—H61A109.3
N6—C22—H22124.8N10—C61—H61B109.3
N6—C23—C28130.4 (3)C62—C61—H61B109.3
N6—C23—C24107.4 (2)H61A—C61—H61B107.9
C28—C23—C24122.2 (3)O15—C62—C61111.0 (2)
C25—C24—C23118.9 (2)O15—C62—H62A109.4
C25—C24—C21134.0 (2)C61—C62—H62A109.4
C23—C24—C21107.1 (2)O15—C62—H62B109.4
C26—C25—C24118.9 (3)C61—C62—H62B109.4
C26—C25—H25120.6H62A—C62—H62B108.0
C24—C25—H25120.6N11—C63—C64111.08 (19)
C25—C26—C27120.6 (3)N11—C63—H63A109.4
C25—C26—H26119.7C64—C63—H63A109.4
C27—C26—H26119.7N11—C63—H63B109.4
C28—C27—C26122.2 (3)C64—C63—H63B109.4
C28—C27—H27118.9H63A—C63—H63B108.0
C26—C27—H27118.9O16—C64—C63112.60 (19)
C27—C28—C23117.2 (3)O16—C64—H64A109.1
C27—C28—H28121.4C63—C64—H64A109.1
C23—C28—H28121.4O16—C64—H64B109.1
N4—C29—C30112.8 (2)C63—C64—H64B109.1
N4—C29—H29A109.0H64A—C64—H64B107.8
C4—N1—C1—O1179.4 (2)C36—N7—C33—O9174.9 (2)
C13—N1—C1—O14.7 (4)C45—N7—C33—O95.6 (4)
C4—N1—C1—C21.2 (2)C36—N7—C33—C345.2 (2)
C13—N1—C1—C2175.9 (2)C45—N7—C33—C34174.5 (2)
C15—N2—C2—C39.9 (4)C47—N8—C34—C3519.5 (4)
C15—N2—C2—C1168.2 (2)C47—N8—C34—C33161.0 (2)
O1—C1—C2—N22.2 (4)O9—C33—C34—N84.4 (4)
N1—C1—C2—N2177.1 (2)N7—C33—C34—N8175.5 (2)
O1—C1—C2—C3179.2 (2)O9—C33—C34—C35175.1 (3)
N1—C1—C2—C31.4 (2)N7—C33—C34—C354.9 (3)
N2—C2—C3—C4177.2 (3)N8—C34—C35—C36177.8 (3)
C1—C2—C3—C41.0 (2)C33—C34—C35—C362.7 (3)
N2—C2—C3—C57.8 (4)N8—C34—C35—C376.9 (5)
C1—C2—C3—C5173.9 (2)C33—C34—C35—C37172.6 (2)
C1—N1—C4—O2179.2 (2)C33—N7—C36—O10175.0 (2)
C13—N1—C4—O24.4 (3)C45—N7—C36—O105.5 (4)
C1—N1—C4—C30.6 (2)C33—N7—C36—C353.7 (3)
C13—N1—C4—C3175.3 (2)C45—N7—C36—C35173.2 (2)
C2—C3—C4—O2179.9 (2)C34—C35—C36—O10178.2 (2)
C5—C3—C4—O24.6 (4)C37—C35—C36—O102.4 (4)
C2—C3—C4—N10.3 (2)C34—C35—C36—N70.4 (3)
C5—C3—C4—N1175.19 (19)C37—C35—C36—N7176.3 (2)
C2—C3—C5—C658.8 (4)C34—C35—C37—C3845.4 (4)
C4—C3—C5—C6115.5 (3)C36—C35—C37—C38129.3 (2)
C2—C3—C5—C8120.0 (3)C34—C35—C37—C40134.2 (3)
C4—C3—C5—C865.7 (3)C36—C35—C37—C4051.1 (3)
C8—C5—C6—N31.8 (3)C39—N9—C38—C371.4 (3)
C3—C5—C6—N3177.2 (2)C40—C37—C38—N92.2 (3)
C7—N3—C6—C51.4 (3)C35—C37—C38—N9177.46 (19)
C6—N3—C7—C12179.8 (3)C38—N9—C39—C44179.7 (2)
C6—N3—C7—C80.3 (3)C38—N9—C39—C400.0 (3)
N3—C7—C8—C9179.0 (2)N9—C39—C40—C41178.0 (2)
C12—C7—C8—C91.4 (4)C44—C39—C40—C411.8 (3)
N3—C7—C8—C50.9 (3)N9—C39—C40—C371.3 (2)
C12—C7—C8—C5178.8 (2)C44—C39—C40—C37179.0 (2)
C6—C5—C8—C9178.2 (3)C38—C37—C40—C41177.0 (2)
C3—C5—C8—C92.8 (4)C35—C37—C40—C413.4 (4)
C6—C5—C8—C71.6 (3)C38—C37—C40—C392.1 (2)
C3—C5—C8—C7177.4 (2)C35—C37—C40—C39177.5 (2)
C7—C8—C9—C100.4 (3)C39—C40—C41—C420.3 (3)
C5—C8—C9—C10179.8 (3)C37—C40—C41—C42178.7 (2)
C8—C9—C10—C110.8 (4)C40—C41—C42—C432.0 (3)
C9—C10—C11—C121.1 (4)C41—C42—C43—C441.7 (4)
C10—C11—C12—C70.2 (4)C42—C43—C44—C390.3 (4)
N3—C7—C12—C11179.4 (3)N9—C39—C44—C43177.6 (2)
C8—C7—C12—C111.1 (4)C40—C39—C44—C432.1 (4)
C1—N1—C13—C1483.0 (3)C33—N7—C45—C4689.9 (3)
C4—N1—C13—C14103.1 (3)C36—N7—C45—C46102.2 (2)
N1—C13—C14—O362.8 (3)N7—C45—C46—O11166.08 (18)
C2—N2—C15—C16108.6 (3)C34—N8—C47—C4860.6 (3)
N2—C15—C16—O470.6 (3)N8—C47—C48—O1260.5 (3)
C20—N4—C17—O5178.5 (2)C52—N10—C49—O13175.2 (2)
C29—N4—C17—O57.6 (4)C61—N10—C49—O137.2 (4)
C20—N4—C17—C182.5 (3)C52—N10—C49—C504.3 (2)
C29—N4—C17—C18173.3 (2)C61—N10—C49—C50172.23 (19)
C31—N5—C18—C1911.6 (4)C63—N11—C50—C5122.0 (4)
C31—N5—C18—C17167.7 (2)C63—N11—C50—C49157.6 (2)
O5—C17—C18—N52.7 (4)O13—C49—C50—N114.3 (4)
N4—C17—C18—N5176.3 (2)N10—C49—C50—N11176.2 (2)
O5—C17—C18—C19177.8 (2)O13—C49—C50—C51176.0 (2)
N4—C17—C18—C193.1 (3)N10—C49—C50—C513.5 (2)
N5—C18—C19—C20176.9 (3)N11—C50—C51—C52178.3 (3)
C17—C18—C19—C202.4 (3)C49—C50—C51—C521.3 (2)
N5—C18—C19—C218.3 (5)N11—C50—C51—C537.0 (4)
C17—C18—C19—C21172.4 (2)C49—C50—C51—C53173.4 (2)
C17—N4—C20—O6177.9 (2)C49—N10—C52—O14175.1 (2)
C29—N4—C20—O67.1 (4)C61—N10—C52—O147.4 (3)
C17—N4—C20—C191.0 (3)C49—N10—C52—C513.6 (3)
C29—N4—C20—C19171.9 (2)C61—N10—C52—C51171.4 (2)
C18—C19—C20—O6179.8 (3)C50—C51—C52—O14177.4 (2)
C21—C19—C20—O64.4 (4)C53—C51—C52—O142.2 (4)
C18—C19—C20—N41.0 (3)C50—C51—C52—N101.3 (2)
C21—C19—C20—N4174.4 (2)C53—C51—C52—N10176.44 (19)
C18—C19—C21—C2257.9 (4)C50—C51—C53—C5443.0 (4)
C20—C19—C21—C22116.2 (3)C52—C51—C53—C54130.9 (3)
C18—C19—C21—C24122.4 (3)C50—C51—C53—C56136.3 (3)
C20—C19—C21—C2463.4 (3)C52—C51—C53—C5649.8 (3)
C24—C21—C22—N61.5 (3)C55—N12—C54—C531.3 (3)
C19—C21—C22—N6178.8 (2)C56—C53—C54—N121.9 (3)
C23—N6—C22—C211.2 (3)C51—C53—C54—N12177.6 (2)
C22—N6—C23—C28179.7 (2)C54—N12—C55—C60179.2 (3)
C22—N6—C23—C240.4 (3)C54—N12—C55—C560.2 (3)
N6—C23—C24—C25180.0 (2)N12—C55—C56—C57178.2 (2)
C28—C23—C24—C250.7 (3)C60—C55—C56—C572.8 (4)
N6—C23—C24—C210.5 (2)N12—C55—C56—C530.9 (3)
C28—C23—C24—C21178.8 (2)C60—C55—C56—C53178.1 (2)
C22—C21—C24—C25179.3 (3)C54—C53—C56—C57177.2 (3)
C19—C21—C24—C250.4 (4)C51—C53—C56—C573.4 (4)
C22—C21—C24—C231.2 (2)C54—C53—C56—C551.7 (3)
C19—C21—C24—C23179.1 (2)C51—C53—C56—C55177.7 (2)
C23—C24—C25—C260.2 (3)C55—C56—C57—C581.3 (4)
C21—C24—C25—C26179.6 (2)C53—C56—C57—C58180.0 (3)
C24—C25—C26—C271.0 (4)C56—C57—C58—C590.5 (4)
C25—C26—C27—C281.0 (4)C57—C58—C59—C601.0 (4)
C26—C27—C28—C230.1 (4)C58—C59—C60—C550.4 (4)
N6—C23—C28—C27179.9 (3)N12—C55—C60—C59178.9 (3)
C24—C23—C28—C270.8 (4)C56—C55—C60—C592.3 (4)
C17—N4—C29—C3077.1 (3)C49—N10—C61—C6280.2 (3)
C20—N4—C29—C30113.5 (3)C52—N10—C61—C62113.8 (2)
N4—C29—C30—O764.3 (3)N10—C61—C62—O15170.44 (18)
C18—N5—C31—C32112.1 (3)C50—N11—C63—C6461.8 (3)
N5—C31—C32—O865.4 (3)N11—C63—C64—O1660.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O12i0.86 (3)2.09 (3)2.950 (3)177 (3)
O3—H3···O8ii0.84 (3)1.93 (3)2.762 (3)172 (3)
O4—H4···O14iii0.82 (2)1.97 (2)2.770 (2)163 (3)
N5—H5···O16iv0.83 (2)2.22 (2)3.027 (3)164 (2)
O7—H7···O4v0.86 (2)1.89 (2)2.755 (3)175 (3)
O15—H15···O1vi0.84 (2)2.22 (2)2.893 (2)137 (3)
O15—H15···O12vii0.84 (2)2.42 (2)3.097 (3)139 (3)
O16—H16···O11i0.83 (2)1.96 (2)2.780 (3)170 (3)
N3—H3A···O6iii0.87 (2)2.06 (2)2.840 (2)149 (2)
N6—H6A···O140.84 (2)2.22 (2)3.042 (3)168 (2)
O8—H8A···O10viii0.85 (2)1.90 (2)2.746 (3)173 (3)
N9—H9A···O2viii0.89 (2)1.95 (2)2.760 (2)152 (2)
O11—H11A···O5ii0.87 (2)2.13 (2)2.935 (2)154 (3)
O11—H11A···O160.87 (2)2.51 (3)3.033 (3)120 (3)
O12—H12A···O15ix0.84 (2)1.92 (2)2.739 (2)168 (3)
N8—H8B···O7x0.89 (2)2.09 (2)2.867 (3)146 (2)
N11—H11B···O30.88 (2)2.17 (2)2.945 (3)147 (2)
N12—H12B···O10viii0.85 (2)2.10 (2)2.925 (2)164 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x1, y, z; (iii) x, y, z+1; (iv) x+1, y, z; (v) x+1, y, z1; (vi) x, y+2, z+1; (vii) x, y+1, z; (viii) x+1, y+1, z+1; (ix) x, y+1, z; (x) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H17N3O4
Mr315.33
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)13.0276 (10), 14.8150 (11), 17.8893 (14)
α, β, γ (°)90.012 (1), 110.295 (2), 102.187 (2)
V3)3155.2 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.43 × 0.33 × 0.27
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.594, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
17464, 12193, 6708
Rint0.035
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.098, 0.89
No. of reflections12193
No. of parameters893
No. of restraints13
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.18

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O12i0.86 (3)2.09 (3)2.950 (3)177 (3)
O3—H3···O8ii0.84 (3)1.93 (3)2.762 (3)172 (3)
O4—H4···O14iii0.822 (17)1.972 (19)2.770 (2)163 (3)
N5—H5···O16iv0.829 (15)2.222 (16)3.027 (3)164 (2)
O7—H7···O4v0.864 (17)1.893 (18)2.755 (3)175 (3)
O15—H15···O1vi0.838 (16)2.22 (2)2.893 (2)137 (3)
O15—H15···O12vii0.838 (16)2.42 (2)3.097 (3)139 (3)
O16—H16···O11i0.831 (17)1.958 (18)2.780 (3)170 (3)
N3—H3A···O6iii0.87 (2)2.06 (2)2.840 (2)149 (2)
N6—H6A···O140.835 (15)2.221 (16)3.042 (3)168 (2)
O8—H8A···O10viii0.846 (18)1.903 (18)2.746 (3)173 (3)
N9—H9A···O2viii0.890 (16)1.945 (19)2.760 (2)152 (2)
O11—H11A···O5ii0.866 (18)2.13 (2)2.935 (2)154 (3)
O11—H11A···O160.866 (18)2.51 (3)3.033 (3)120 (3)
O12—H12A···O15ix0.836 (16)1.915 (17)2.739 (2)168 (3)
N8—H8B···O7x0.886 (15)2.090 (17)2.867 (3)145.9 (18)
N11—H11B···O30.878 (15)2.17 (2)2.945 (3)147 (2)
N12—H12B···O10viii0.848 (15)2.101 (16)2.925 (2)164 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x1, y, z; (iii) x, y, z+1; (iv) x+1, y, z; (v) x+1, y, z1; (vi) x, y+2, z+1; (vii) x, y+1, z; (viii) x+1, y+1, z+1; (ix) x, y+1, z; (x) x+1, y+1, z.
 

Acknowledgements

We thank the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry of China (No. [2008]890) for financial support.

References

First citationBruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHu, H. (1996). Drug Discov. Today, 1, 438–447.  CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationVegesna, R. V., Wu, H. L., Mong, S. & Crooke, S. T. (1998). Mol. Pharmacol. 33, 537–542.
First citationZhao, S. Y., Jiang, D. F., Yang, Y. W. & Shao, Z. Y. (2010). Lett. Org. Chem. 7, 144–148.
First citationZhao, S. Y., Shao, Z. Y., Qin, W. M. & Zhang, D. Q. (2008). Chin. J. Org. Chem. 28, 1128–1137.

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