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

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ISSN: 2056-9890

Ethyl {6-[6-(eth­oxy­carbon­yl)picolin­amido­carbon­yl]picolinamido­carbon­yl}picolinate

aBeijing National Laboratory for Molecular Sciences (BNLMS), Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China, and Graduate University of the Chinese Academy of Sciences (GUCAS), Beijing 100049, People's Republic of China
*Correspondence e-mail: jnyao@iccas.ac.cn

(Received 24 November 2008; accepted 4 December 2008; online 10 December 2008)

The title mol­ecule, C25H21N5O8, adopts a helical conformation, which is stabilized by two intra­molecular bifurcated N—H⋯(N,N) hydrogen bonds.

Related literature

For a review on aromatic oligoamides (AOAs), see, for example: Huc (2004[Huc, I. (2004). Eur. J. Org. Chem. pp. 17-29.]). For related compounds, see: Li et al. (2008[Li, X., Zhan, C., Wang, Y. & Yao, J. (2008). Chem. Commun. pp. 2444-2446.]).

[Scheme 1]

Experimental

Crystal data
  • C25H21N5O8

  • Mr = 519.47

  • Monoclinic, P 21 /c

  • a = 7.4952 (8) Å

  • b = 19.998 (2) Å

  • c = 15.9966 (17) Å

  • β = 96.376 (1)°

  • V = 2382.8 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 113 (2) K

  • 0.32 × 0.22 × 0.18 mm

Data collection
  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalcClear; Rigaku, 1999[Rigaku (1999). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.966, Tmax = 0.980

  • 30537 measured reflections

  • 6101 independent reflections

  • 5457 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.096

  • S = 1.08

  • 6101 reflections

  • 354 parameters

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

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4—H4⋯N3 0.885 (14) 2.153 (14) 2.6131 (13) 111.7 (11)
N4—H4⋯N5 0.885 (14) 2.158 (14) 2.6297 (12) 112.8 (11)
N2—H2⋯N3 0.878 (15) 2.148 (14) 2.6006 (12) 111.4 (11)
N2—H2⋯N1 0.878 (15) 2.151 (14) 2.6329 (12) 114.0 (11)

Data collection: CrystalClear (Rigaku, 1999[Rigaku (1999). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku, 1999[Rigaku (1999). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Comment top

The stucture of the title compound is shown in Fig. 1. Dimensions are available in the archived CIF. The hydrogen bonds are listed in Table 1. For background, see for example: Huc (2004). For related compounds, see: Li et al. (2008).

Related literature top

For a review on aromatic oligoamides (AOAs), see, for example: Huc (2004). For related compounds, see: Li et al. (2008).

Experimental top

The title compound was obtained from 2-ethoxycarbonyl- 6-pyridinoyl amide and 2,6-pyridinoyl dichloride and recrystallised from DMF/ethyl ether to yield colourless prisms of (I).

Refinement top

The N-bound hydrogen atoms were located in a difference map and freely refined. The C-bound hydrogen atoms were geometrically placed (C—H = 0.95–0.99Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalClear (Rigaku, 1999); 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: CrystalStructure (Rigaku, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids for the non-hydrogen atoms. The hydrogen bonds are shown as double-dashed lines.
[Figure 2] Fig. 2. The formation of the title compound.
Ethyl {6-[6-(ethoxycarbonyl)picolinamidocarbonyl]picolinamidocarbonyl}picolinate top
Crystal data top
C25H21N5O8F(000) = 1080
Mr = 519.47Dx = 1.448 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 6439 reflections
a = 7.4952 (8) Åθ = 2.6–26.0°
b = 19.998 (2) ŵ = 0.11 mm1
c = 15.9966 (17) ÅT = 113 K
β = 96.376 (1)°Prism, colorless
V = 2382.8 (4) Å30.32 × 0.22 × 0.18 mm
Z = 4
Data collection top
Rigaku Saturn
diffractometer
6101 independent reflections
Radiation source: rotating anode5457 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.025
Detector resolution: 7.31 pixels mm-1θmax = 28.7°, θmin = 2.4°
ω scansh = 1010
Absorption correction: multi-scan
(CrystalcClear; Rigaku, 1999)
k = 2724
Tmin = 0.966, Tmax = 0.980l = 2121
30537 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0481P)2 + 0.4996P]
where P = (Fo2 + 2Fc2)/3
6101 reflections(Δ/σ)max = 0.001
354 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C25H21N5O8V = 2382.8 (4) Å3
Mr = 519.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.4952 (8) ŵ = 0.11 mm1
b = 19.998 (2) ÅT = 113 K
c = 15.9966 (17) Å0.32 × 0.22 × 0.18 mm
β = 96.376 (1)°
Data collection top
Rigaku Saturn
diffractometer
6101 independent reflections
Absorption correction: multi-scan
(CrystalcClear; Rigaku, 1999)
5457 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.980Rint = 0.025
30537 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.32 e Å3
6101 reflectionsΔρmin = 0.17 e Å3
354 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
O10.13320 (11)0.87694 (4)0.72665 (5)0.02977 (17)
O20.06124 (11)0.85871 (4)0.63149 (5)0.02910 (17)
O30.16781 (12)0.59423 (4)0.88294 (6)0.0395 (2)
O40.33384 (11)0.65393 (4)1.02334 (5)0.03521 (19)
O50.24510 (13)0.99672 (4)0.94666 (5)0.0397 (2)
O60.08420 (13)1.00415 (4)0.86648 (5)0.0391 (2)
O70.21781 (10)0.70449 (4)0.93765 (4)0.02615 (16)
O80.37042 (9)0.67410 (4)0.82982 (4)0.02587 (16)
N10.10247 (10)0.74283 (4)0.76977 (5)0.02135 (16)
N20.21026 (12)0.70511 (4)0.91366 (5)0.02446 (18)
N30.25843 (11)0.82284 (4)0.97648 (5)0.02253 (17)
N40.04508 (12)0.91296 (4)0.92339 (5)0.02641 (18)
N50.20551 (11)0.83332 (4)0.87730 (5)0.02099 (16)
C10.04508 (13)0.83975 (5)0.68831 (6)0.02336 (19)
C20.03851 (12)0.76501 (5)0.70001 (6)0.02167 (19)
C30.02896 (13)0.72245 (5)0.64172 (6)0.0245 (2)
H30.07640.74000.59360.029*
C40.02507 (13)0.65399 (5)0.65576 (6)0.0264 (2)
H4A0.06570.62370.61620.032*
C50.03894 (13)0.63047 (5)0.72829 (7)0.0262 (2)
H50.04190.58390.73980.031*
C60.09874 (12)0.67674 (5)0.78370 (6)0.02280 (19)
C70.16141 (13)0.65290 (5)0.86502 (7)0.0260 (2)
C80.29462 (13)0.70359 (5)0.98611 (6)0.0248 (2)
C90.34013 (13)0.77315 (5)1.01301 (6)0.0241 (2)
C100.46393 (14)0.78407 (7)1.07012 (7)0.0334 (2)
H100.51800.74781.09610.040*
C110.50571 (15)0.84953 (7)1.08782 (8)0.0400 (3)
H110.59040.85881.12630.048*
C120.42408 (15)0.90164 (6)1.04950 (7)0.0353 (3)
H120.45300.94681.06030.042*
C130.29831 (14)0.88586 (5)0.99470 (6)0.0263 (2)
C140.19693 (15)0.93888 (5)0.95273 (6)0.0287 (2)
C150.08115 (15)0.94475 (5)0.88163 (6)0.0272 (2)
C160.22015 (13)0.89727 (5)0.85479 (6)0.0240 (2)
C170.35075 (15)0.92050 (6)0.80694 (7)0.0318 (2)
H170.35870.96670.79390.038*
C180.46885 (15)0.87489 (6)0.77877 (8)0.0350 (3)
H180.56030.88920.74620.042*
C190.45178 (14)0.80778 (6)0.79891 (7)0.0290 (2)
H190.52860.77510.77880.035*
C200.31961 (12)0.78940 (5)0.84913 (6)0.02153 (19)
C210.29545 (12)0.71868 (5)0.87815 (6)0.02146 (19)
C220.06263 (18)0.92999 (5)0.61175 (7)0.0342 (2)
H22A0.08270.95680.66400.041*
H22B0.05320.94350.58060.041*
C230.2126 (2)0.94046 (6)0.55884 (9)0.0482 (4)
H23A0.32670.92820.59120.072*
H23B0.21630.98760.54230.072*
H23C0.19310.91240.50840.072*
C240.35652 (15)0.60428 (5)0.85650 (7)0.0275 (2)
H24A0.23150.59410.86660.033*
H24B0.43560.59650.90940.033*
C250.41238 (17)0.56010 (6)0.78771 (7)0.0352 (2)
H25A0.32900.56620.73660.053*
H25B0.41040.51330.80560.053*
H25C0.53410.57210.77620.053*
H40.0313 (18)0.8692 (7)0.9284 (8)0.036 (4)*
H20.1908 (19)0.7449 (8)0.8932 (9)0.040 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0356 (4)0.0277 (4)0.0269 (4)0.0077 (3)0.0077 (3)0.0011 (3)
O20.0378 (4)0.0242 (4)0.0268 (4)0.0026 (3)0.0104 (3)0.0007 (3)
O30.0507 (5)0.0201 (4)0.0503 (5)0.0036 (3)0.0176 (4)0.0003 (3)
O40.0350 (4)0.0360 (4)0.0355 (4)0.0062 (3)0.0075 (3)0.0099 (3)
O50.0549 (5)0.0247 (4)0.0386 (5)0.0185 (4)0.0005 (4)0.0020 (3)
O60.0650 (6)0.0165 (4)0.0358 (4)0.0003 (4)0.0059 (4)0.0058 (3)
O70.0308 (4)0.0222 (4)0.0266 (4)0.0031 (3)0.0085 (3)0.0035 (3)
O80.0267 (4)0.0239 (4)0.0280 (4)0.0045 (3)0.0076 (3)0.0009 (3)
N10.0193 (4)0.0215 (4)0.0231 (4)0.0004 (3)0.0013 (3)0.0035 (3)
N20.0272 (4)0.0203 (4)0.0269 (4)0.0018 (3)0.0075 (3)0.0004 (3)
N30.0231 (4)0.0256 (4)0.0186 (4)0.0055 (3)0.0007 (3)0.0008 (3)
N40.0374 (5)0.0147 (4)0.0277 (4)0.0050 (3)0.0059 (3)0.0009 (3)
N50.0218 (4)0.0188 (4)0.0218 (4)0.0021 (3)0.0004 (3)0.0022 (3)
C10.0249 (5)0.0267 (5)0.0179 (4)0.0022 (4)0.0001 (3)0.0014 (3)
C20.0187 (4)0.0245 (5)0.0211 (4)0.0011 (3)0.0011 (3)0.0036 (3)
C30.0209 (4)0.0301 (5)0.0218 (4)0.0016 (4)0.0001 (3)0.0058 (4)
C40.0223 (4)0.0286 (5)0.0278 (5)0.0021 (4)0.0002 (4)0.0109 (4)
C50.0234 (5)0.0220 (5)0.0325 (5)0.0012 (4)0.0005 (4)0.0084 (4)
C60.0194 (4)0.0218 (5)0.0269 (5)0.0022 (3)0.0013 (3)0.0053 (4)
C70.0241 (5)0.0208 (5)0.0334 (5)0.0028 (4)0.0052 (4)0.0024 (4)
C80.0197 (4)0.0309 (5)0.0239 (5)0.0021 (4)0.0020 (3)0.0026 (4)
C90.0190 (4)0.0340 (5)0.0189 (4)0.0008 (4)0.0009 (3)0.0006 (4)
C100.0233 (5)0.0522 (7)0.0254 (5)0.0044 (5)0.0061 (4)0.0067 (5)
C110.0255 (5)0.0603 (8)0.0357 (6)0.0018 (5)0.0099 (4)0.0177 (6)
C120.0280 (5)0.0441 (7)0.0332 (6)0.0112 (5)0.0014 (4)0.0141 (5)
C130.0260 (5)0.0299 (5)0.0218 (4)0.0099 (4)0.0017 (4)0.0048 (4)
C140.0375 (6)0.0245 (5)0.0231 (5)0.0103 (4)0.0013 (4)0.0029 (4)
C150.0412 (6)0.0179 (4)0.0219 (4)0.0010 (4)0.0004 (4)0.0022 (3)
C160.0281 (5)0.0200 (5)0.0230 (4)0.0040 (4)0.0017 (4)0.0036 (3)
C170.0330 (5)0.0279 (5)0.0338 (5)0.0085 (4)0.0005 (4)0.0108 (4)
C180.0250 (5)0.0423 (7)0.0383 (6)0.0051 (4)0.0060 (4)0.0166 (5)
C190.0203 (4)0.0365 (6)0.0304 (5)0.0028 (4)0.0040 (4)0.0096 (4)
C200.0183 (4)0.0236 (5)0.0220 (4)0.0000 (3)0.0007 (3)0.0037 (3)
C210.0180 (4)0.0229 (5)0.0229 (4)0.0024 (3)0.0001 (3)0.0015 (3)
C220.0510 (7)0.0238 (5)0.0287 (5)0.0041 (5)0.0082 (5)0.0031 (4)
C230.0808 (10)0.0273 (6)0.0419 (7)0.0084 (6)0.0309 (7)0.0045 (5)
C240.0320 (5)0.0221 (5)0.0288 (5)0.0063 (4)0.0056 (4)0.0017 (4)
C250.0420 (6)0.0298 (6)0.0350 (6)0.0093 (5)0.0095 (5)0.0033 (4)
Geometric parameters (Å, º) top
O1—C11.2064 (12)C8—C91.5063 (15)
O2—C11.3289 (12)C9—C101.3898 (14)
O2—C221.4603 (13)C10—C111.3825 (18)
O3—C71.2100 (13)C10—H100.9500
O4—C81.2109 (13)C11—C121.3854 (19)
O5—C141.2123 (13)C11—H110.9500
O6—C151.2131 (13)C12—C131.3930 (15)
O7—C211.2034 (12)C12—H120.9500
O8—C211.3434 (12)C13—C141.5052 (16)
O8—C241.4671 (12)C15—C161.5068 (15)
N1—C21.3382 (13)C16—C171.3880 (15)
N1—C61.3401 (13)C17—C181.3809 (17)
N2—C71.3760 (13)C17—H170.9500
N2—C81.3809 (13)C18—C191.3893 (16)
N2—H20.878 (15)C18—H180.9500
N3—C131.3348 (13)C19—C201.3924 (14)
N3—C91.3354 (13)C19—H190.9500
N4—C151.3732 (14)C20—C211.5057 (13)
N4—C141.3796 (14)C22—C231.4949 (18)
N4—H40.885 (14)C22—H22A0.9900
N5—C161.3364 (12)C22—H22B0.9900
N5—C201.3384 (13)C23—H23A0.9800
C1—C21.5064 (14)C23—H23B0.9800
C2—C31.3979 (13)C23—H23C0.9800
C3—C41.3882 (15)C24—C251.5064 (14)
C3—H30.9500C24—H24A0.9900
C4—C51.3859 (15)C24—H24B0.9900
C4—H4A0.9500C25—H25A0.9800
C5—C61.3895 (14)C25—H25B0.9800
C5—H50.9500C25—H25C0.9800
C6—C71.5086 (14)
C1—O2—C22116.47 (8)C12—C13—C14122.10 (10)
C21—O8—C24114.60 (8)O5—C14—N4125.50 (11)
C2—N1—C6117.56 (8)O5—C14—C13123.18 (10)
C7—N2—C8129.30 (9)N4—C14—C13111.32 (8)
C7—N2—H2114.2 (9)O6—C15—N4125.43 (11)
C8—N2—H2116.3 (9)O6—C15—C16122.08 (10)
C13—N3—C9118.83 (9)N4—C15—C16112.49 (8)
C15—N4—C14129.10 (9)N5—C16—C17123.57 (10)
C15—N4—H4115.0 (9)N5—C16—C15116.50 (9)
C14—N4—H4115.7 (9)C17—C16—C15119.90 (9)
C16—N5—C20117.56 (9)C18—C17—C16118.41 (10)
O1—C1—O2125.14 (10)C18—C17—H17120.8
O1—C1—C2124.11 (9)C16—C17—H17120.8
O2—C1—C2110.75 (8)C17—C18—C19118.91 (10)
N1—C2—C3122.96 (9)C17—C18—H18120.5
N1—C2—C1114.99 (8)C19—C18—H18120.5
C3—C2—C1122.04 (9)C18—C19—C20118.59 (10)
C4—C3—C2118.48 (10)C18—C19—H19120.7
C4—C3—H3120.8C20—C19—H19120.7
C2—C3—H3120.8N5—C20—C19122.90 (9)
C5—C4—C3119.04 (9)N5—C20—C21114.16 (8)
C5—C4—H4A120.5C19—C20—C21122.92 (9)
C3—C4—H4A120.5O7—C21—O8124.66 (9)
C4—C5—C6118.31 (10)O7—C21—C20123.41 (9)
C4—C5—H5120.8O8—C21—C20111.94 (8)
C6—C5—H5120.8O2—C22—C23106.44 (9)
N1—C6—C5123.57 (9)O2—C22—H22A110.4
N1—C6—C7116.89 (8)C23—C22—H22A110.4
C5—C6—C7119.53 (9)O2—C22—H22B110.4
O3—C7—N2125.58 (10)C23—C22—H22B110.4
O3—C7—C6122.35 (9)H22A—C22—H22B108.6
N2—C7—C6112.06 (8)C22—C23—H23A109.5
O4—C8—N2126.13 (10)C22—C23—H23B109.5
O4—C8—C9122.81 (9)H23A—C23—H23B109.5
N2—C8—C9111.02 (8)C22—C23—H23C109.5
N3—C9—C10122.87 (10)H23A—C23—H23C109.5
N3—C9—C8115.64 (8)H23B—C23—H23C109.5
C10—C9—C8121.45 (10)O8—C24—C25108.13 (8)
C11—C10—C9117.80 (11)O8—C24—H24A110.1
C11—C10—H10121.1C25—C24—H24A110.1
C9—C10—H10121.1O8—C24—H24B110.1
C10—C11—C12120.02 (10)C25—C24—H24B110.1
C10—C11—H11120.0H24A—C24—H24B108.4
C12—C11—H11120.0C24—C25—H25A109.5
C11—C12—C13118.10 (11)C24—C25—H25B109.5
C11—C12—H12121.0H25A—C25—H25B109.5
C13—C12—H12121.0C24—C25—H25C109.5
N3—C13—C12122.34 (11)H25A—C25—H25C109.5
N3—C13—C14115.55 (9)H25B—C25—H25C109.5
C22—O2—C1—O13.25 (15)C9—N3—C13—C120.98 (14)
C22—O2—C1—C2177.85 (8)C9—N3—C13—C14178.44 (8)
C6—N1—C2—C30.73 (13)C11—C12—C13—N31.89 (16)
C6—N1—C2—C1179.54 (8)C11—C12—C13—C14177.48 (10)
O1—C1—C2—N115.36 (14)C15—N4—C14—O50.58 (18)
O2—C1—C2—N1163.55 (8)C15—N4—C14—C13179.72 (9)
O1—C1—C2—C3164.37 (10)N3—C13—C14—O5162.22 (10)
O2—C1—C2—C316.71 (12)C12—C13—C14—O518.36 (16)
N1—C2—C3—C41.73 (14)N3—C13—C14—N418.07 (12)
C1—C2—C3—C4177.98 (8)C12—C13—C14—N4161.35 (9)
C2—C3—C4—C52.40 (14)C14—N4—C15—O63.77 (18)
C3—C4—C5—C60.72 (14)C14—N4—C15—C16175.83 (9)
C2—N1—C6—C52.58 (14)C20—N5—C16—C172.57 (14)
C2—N1—C6—C7176.59 (8)C20—N5—C16—C15175.38 (8)
C4—C5—C6—N11.87 (15)O6—C15—C16—N5178.10 (10)
C4—C5—C6—C7177.27 (9)N4—C15—C16—N52.29 (12)
C8—N2—C7—O38.40 (18)O6—C15—C16—C173.88 (15)
C8—N2—C7—C6170.93 (9)N4—C15—C16—C17175.74 (9)
N1—C6—C7—O3178.12 (10)N5—C16—C17—C182.05 (16)
C5—C6—C7—O32.68 (15)C15—C16—C17—C18175.83 (10)
N1—C6—C7—N21.24 (12)C16—C17—C18—C190.37 (16)
C5—C6—C7—N2177.96 (9)C17—C18—C19—C202.07 (16)
C7—N2—C8—O44.13 (18)C16—N5—C20—C190.70 (14)
C7—N2—C8—C9173.76 (9)C16—N5—C20—C21179.34 (8)
C13—N3—C9—C100.73 (14)C18—C19—C20—N51.58 (15)
C13—N3—C9—C8177.19 (8)C18—C19—C20—C21176.94 (9)
O4—C8—C9—N3167.30 (9)C24—O8—C21—O71.92 (13)
N2—C8—C9—N314.72 (12)C24—O8—C21—C20178.12 (8)
O4—C8—C9—C1014.75 (15)N5—C20—C21—O719.00 (13)
N2—C8—C9—C10163.23 (9)C19—C20—C21—O7159.64 (10)
N3—C9—C10—C111.43 (15)N5—C20—C21—O8160.96 (8)
C8—C9—C10—C11176.37 (10)C19—C20—C21—O820.40 (13)
C9—C10—C11—C120.44 (17)C1—O2—C22—C23170.48 (10)
C10—C11—C12—C131.12 (17)C21—O8—C24—C25168.94 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···N30.885 (14)2.153 (14)2.6131 (13)111.7 (11)
N4—H4···N50.885 (14)2.158 (14)2.6297 (12)112.8 (11)
N2—H2···N30.878 (15)2.148 (14)2.6006 (12)111.4 (11)
N2—H2···N10.878 (15)2.151 (14)2.6329 (12)114.0 (11)

Experimental details

Crystal data
Chemical formulaC25H21N5O8
Mr519.47
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)7.4952 (8), 19.998 (2), 15.9966 (17)
β (°) 96.376 (1)
V3)2382.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.32 × 0.22 × 0.18
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
(CrystalcClear; Rigaku, 1999)
Tmin, Tmax0.966, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
30537, 6101, 5457
Rint0.025
(sin θ/λ)max1)0.676
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.096, 1.08
No. of reflections6101
No. of parameters354
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.17

Computer programs: CrystalClear (Rigaku, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···N30.885 (14)2.153 (14)2.6131 (13)111.7 (11)
N4—H4···N50.885 (14)2.158 (14)2.6297 (12)112.8 (11)
N2—H2···N30.878 (15)2.148 (14)2.6006 (12)111.4 (11)
N2—H2···N10.878 (15)2.151 (14)2.6329 (12)114.0 (11)
 

Acknowledgements

We thank the NSFC (Nos. 50221201, 20872145, 20733006), the Chinese Academy of Sciences and the National Research Fund for Fundamental Key Project 973 (2006CB806200, 2007CB936401) for support.

References

First citationHuc, I. (2004). Eur. J. Org. Chem. pp. 17-29.  Web of Science CrossRef Google Scholar
First citationLi, X., Zhan, C., Wang, Y. & Yao, J. (2008). Chem. Commun. pp. 2444–2446.  Web of Science CrossRef Google Scholar
First citationRigaku (1999). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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