Acta Cryst. (2009). E65, o51 [ doi:10.1107/S1600536808040932 ]
The title molecule, C25H21N5O8, adopts a helical conformation, which is stabilized by two intramolecular bifurcated N-H
(N,N) hydrogen bonds.
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).
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).
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).
![[Figure 1]](./hb2864fig1thm.gif)
| 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]](./hb2864fig2thm.gif)
| Fig. 2. The formation of the title compound. |
| C25H21N5O8 | F(000) = 1080 |
| Mr = 519.47 | Dx = 1.448 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71070 Å |
| Hall symbol: -P 2ybc | Cell parameters from 6439 reflections |
| a = 7.4952 (8) Å | θ = 2.6–26.0° |
| b = 19.998 (2) Å | µ = 0.11 mm−1 |
| c = 15.9966 (17) Å | T = 113 K |
| β = 96.376 (1)° | Prism, colorless |
| V = 2382.8 (4) Å3 | 0.32 × 0.22 × 0.18 mm |
| Z = 4 |
| Rigaku Saturn diffractometer | 6101 independent reflections |
| Radiation source: rotating anode | 5457 reflections with I > 2σ(I) |
| confocal | Rint = 0.025 |
| Detector resolution: 7.31 pixels mm-1 | θmax = 28.7°, θmin = 2.4° |
| ω scans | h = −10→10 |
| Absorption correction: multi-scan (CrystalcClear; Rigaku, 1999) | k = −27→24 |
| Tmin = 0.966, Tmax = 0.980 | l = −21→21 |
| 30537 measured reflections |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.096 | H 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 parameters | Δρmax = 0.32 e Å−3 |
| 0 restraints | Δρmin = −0.17 e Å−3 |
| C25H21N5O8 | V = 2382.8 (4) Å3 |
| Mr = 519.47 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 7.4952 (8) Å | µ = 0.11 mm−1 |
| b = 19.998 (2) Å | T = 113 K |
| c = 15.9966 (17) Å | 0.32 × 0.22 × 0.18 mm |
| β = 96.376 (1)° |
| Rigaku Saturn diffractometer | 6101 independent reflections |
| Absorption correction: multi-scan (CrystalcClear; Rigaku, 1999) | 5457 reflections with I > 2σ(I) |
| Tmin = 0.966, Tmax = 0.980 | Rint = 0.025 |
| 30537 measured reflections | θmax = 28.7° |
| R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.096 | Δρmax = 0.32 e Å−3 |
| S = 1.08 | Δρmin = −0.17 e Å−3 |
| 6101 reflections | Absolute structure: ? |
| 354 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | −0.13320 (11) | 0.87694 (4) | 0.72665 (5) | 0.02977 (17) | |
| O2 | 0.06124 (11) | 0.85871 (4) | 0.63149 (5) | 0.02910 (17) | |
| O3 | −0.16781 (12) | 0.59423 (4) | 0.88294 (6) | 0.0395 (2) | |
| O4 | −0.33384 (11) | 0.65393 (4) | 1.02334 (5) | 0.03521 (19) | |
| O5 | −0.24510 (13) | 0.99672 (4) | 0.94666 (5) | 0.0397 (2) | |
| O6 | 0.08420 (13) | 1.00415 (4) | 0.86648 (5) | 0.0391 (2) | |
| O7 | 0.21781 (10) | 0.70449 (4) | 0.93765 (4) | 0.02615 (16) | |
| O8 | 0.37042 (9) | 0.67410 (4) | 0.82982 (4) | 0.02587 (16) | |
| N1 | −0.10247 (10) | 0.74283 (4) | 0.76977 (5) | 0.02135 (16) | |
| N2 | −0.21026 (12) | 0.70511 (4) | 0.91366 (5) | 0.02446 (18) | |
| N3 | −0.25843 (11) | 0.82284 (4) | 0.97648 (5) | 0.02253 (17) | |
| N4 | −0.04508 (12) | 0.91296 (4) | 0.92339 (5) | 0.02641 (18) | |
| N5 | 0.20551 (11) | 0.83332 (4) | 0.87730 (5) | 0.02099 (16) | |
| C1 | −0.04508 (13) | 0.83975 (5) | 0.68831 (6) | 0.02336 (19) | |
| C2 | −0.03851 (12) | 0.76501 (5) | 0.70001 (6) | 0.02167 (19) | |
| C3 | 0.02896 (13) | 0.72245 (5) | 0.64172 (6) | 0.0245 (2) | |
| H3 | 0.0764 | 0.7400 | 0.5936 | 0.029* | |
| C4 | 0.02507 (13) | 0.65399 (5) | 0.65576 (6) | 0.0264 (2) | |
| H4A | 0.0657 | 0.6237 | 0.6162 | 0.032* | |
| C5 | −0.03894 (13) | 0.63047 (5) | 0.72829 (7) | 0.0262 (2) | |
| H5 | −0.0419 | 0.5839 | 0.7398 | 0.031* | |
| C6 | −0.09874 (12) | 0.67674 (5) | 0.78370 (6) | 0.02280 (19) | |
| C7 | −0.16141 (13) | 0.65290 (5) | 0.86502 (7) | 0.0260 (2) | |
| C8 | −0.29462 (13) | 0.70359 (5) | 0.98611 (6) | 0.0248 (2) | |
| C9 | −0.34013 (13) | 0.77315 (5) | 1.01301 (6) | 0.0241 (2) | |
| C10 | −0.46393 (14) | 0.78407 (7) | 1.07012 (7) | 0.0334 (2) | |
| H10 | −0.5180 | 0.7478 | 1.0961 | 0.040* | |
| C11 | −0.50571 (15) | 0.84953 (7) | 1.08782 (8) | 0.0400 (3) | |
| H11 | −0.5904 | 0.8588 | 1.1263 | 0.048* | |
| C12 | −0.42408 (15) | 0.90164 (6) | 1.04950 (7) | 0.0353 (3) | |
| H12 | −0.4530 | 0.9468 | 1.0603 | 0.042* | |
| C13 | −0.29831 (14) | 0.88586 (5) | 0.99470 (6) | 0.0263 (2) | |
| C14 | −0.19693 (15) | 0.93888 (5) | 0.95273 (6) | 0.0287 (2) | |
| C15 | 0.08115 (15) | 0.94475 (5) | 0.88163 (6) | 0.0272 (2) | |
| C16 | 0.22015 (13) | 0.89727 (5) | 0.85479 (6) | 0.0240 (2) | |
| C17 | 0.35075 (15) | 0.92050 (6) | 0.80694 (7) | 0.0318 (2) | |
| H17 | 0.3587 | 0.9667 | 0.7939 | 0.038* | |
| C18 | 0.46885 (15) | 0.87489 (6) | 0.77877 (8) | 0.0350 (3) | |
| H18 | 0.5603 | 0.8892 | 0.7462 | 0.042* | |
| C19 | 0.45178 (14) | 0.80778 (6) | 0.79891 (7) | 0.0290 (2) | |
| H19 | 0.5286 | 0.7751 | 0.7788 | 0.035* | |
| C20 | 0.31961 (12) | 0.78940 (5) | 0.84913 (6) | 0.02153 (19) | |
| C21 | 0.29545 (12) | 0.71868 (5) | 0.87815 (6) | 0.02146 (19) | |
| C22 | 0.06263 (18) | 0.92999 (5) | 0.61175 (7) | 0.0342 (2) | |
| H22A | 0.0827 | 0.9568 | 0.6640 | 0.041* | |
| H22B | −0.0532 | 0.9435 | 0.5806 | 0.041* | |
| C23 | 0.2126 (2) | 0.94046 (6) | 0.55884 (9) | 0.0482 (4) | |
| H23A | 0.3267 | 0.9282 | 0.5912 | 0.072* | |
| H23B | 0.2163 | 0.9876 | 0.5423 | 0.072* | |
| H23C | 0.1931 | 0.9124 | 0.5084 | 0.072* | |
| C24 | 0.35652 (15) | 0.60428 (5) | 0.85650 (7) | 0.0275 (2) | |
| H24A | 0.2315 | 0.5941 | 0.8666 | 0.033* | |
| H24B | 0.4356 | 0.5965 | 0.9094 | 0.033* | |
| C25 | 0.41238 (17) | 0.56010 (6) | 0.78771 (7) | 0.0352 (2) | |
| H25A | 0.3290 | 0.5662 | 0.7366 | 0.053* | |
| H25B | 0.4104 | 0.5133 | 0.8056 | 0.053* | |
| H25C | 0.5341 | 0.5721 | 0.7762 | 0.053* | |
| H4 | −0.0313 (18) | 0.8692 (7) | 0.9284 (8) | 0.036 (4)* | |
| H2 | −0.1908 (19) | 0.7449 (8) | 0.8932 (9) | 0.040 (4)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0356 (4) | 0.0277 (4) | 0.0269 (4) | 0.0077 (3) | 0.0077 (3) | −0.0011 (3) |
| O2 | 0.0378 (4) | 0.0242 (4) | 0.0268 (4) | 0.0026 (3) | 0.0104 (3) | 0.0007 (3) |
| O3 | 0.0507 (5) | 0.0201 (4) | 0.0503 (5) | −0.0036 (3) | 0.0176 (4) | 0.0003 (3) |
| O4 | 0.0350 (4) | 0.0360 (4) | 0.0355 (4) | −0.0062 (3) | 0.0075 (3) | 0.0099 (3) |
| O5 | 0.0549 (5) | 0.0247 (4) | 0.0386 (5) | 0.0185 (4) | 0.0005 (4) | −0.0020 (3) |
| O6 | 0.0650 (6) | 0.0165 (4) | 0.0358 (4) | −0.0003 (4) | 0.0059 (4) | 0.0058 (3) |
| O7 | 0.0308 (4) | 0.0222 (4) | 0.0266 (4) | 0.0031 (3) | 0.0085 (3) | 0.0035 (3) |
| O8 | 0.0267 (4) | 0.0239 (4) | 0.0280 (4) | 0.0045 (3) | 0.0076 (3) | 0.0009 (3) |
| N1 | 0.0193 (4) | 0.0215 (4) | 0.0231 (4) | −0.0004 (3) | 0.0013 (3) | −0.0035 (3) |
| N2 | 0.0272 (4) | 0.0203 (4) | 0.0269 (4) | −0.0018 (3) | 0.0075 (3) | 0.0004 (3) |
| N3 | 0.0231 (4) | 0.0256 (4) | 0.0186 (4) | 0.0055 (3) | 0.0007 (3) | −0.0008 (3) |
| N4 | 0.0374 (5) | 0.0147 (4) | 0.0277 (4) | 0.0050 (3) | 0.0059 (3) | 0.0009 (3) |
| N5 | 0.0218 (4) | 0.0188 (4) | 0.0218 (4) | −0.0021 (3) | −0.0004 (3) | 0.0022 (3) |
| C1 | 0.0249 (5) | 0.0267 (5) | 0.0179 (4) | 0.0022 (4) | 0.0001 (3) | −0.0014 (3) |
| C2 | 0.0187 (4) | 0.0245 (5) | 0.0211 (4) | 0.0011 (3) | −0.0011 (3) | −0.0036 (3) |
| C3 | 0.0209 (4) | 0.0301 (5) | 0.0218 (4) | 0.0016 (4) | 0.0001 (3) | −0.0058 (4) |
| C4 | 0.0223 (4) | 0.0286 (5) | 0.0278 (5) | 0.0021 (4) | −0.0002 (4) | −0.0109 (4) |
| C5 | 0.0234 (5) | 0.0220 (5) | 0.0325 (5) | −0.0012 (4) | 0.0005 (4) | −0.0084 (4) |
| C6 | 0.0194 (4) | 0.0218 (5) | 0.0269 (5) | −0.0022 (3) | 0.0013 (3) | −0.0053 (4) |
| C7 | 0.0241 (5) | 0.0208 (5) | 0.0334 (5) | −0.0028 (4) | 0.0052 (4) | −0.0024 (4) |
| C8 | 0.0197 (4) | 0.0309 (5) | 0.0239 (5) | −0.0021 (4) | 0.0020 (3) | 0.0026 (4) |
| C9 | 0.0190 (4) | 0.0340 (5) | 0.0189 (4) | 0.0008 (4) | 0.0009 (3) | −0.0006 (4) |
| C10 | 0.0233 (5) | 0.0522 (7) | 0.0254 (5) | −0.0044 (5) | 0.0061 (4) | −0.0067 (5) |
| C11 | 0.0255 (5) | 0.0603 (8) | 0.0357 (6) | 0.0018 (5) | 0.0099 (4) | −0.0177 (6) |
| C12 | 0.0280 (5) | 0.0441 (7) | 0.0332 (6) | 0.0112 (5) | 0.0014 (4) | −0.0141 (5) |
| C13 | 0.0260 (5) | 0.0299 (5) | 0.0218 (4) | 0.0099 (4) | −0.0017 (4) | −0.0048 (4) |
| C14 | 0.0375 (6) | 0.0245 (5) | 0.0231 (5) | 0.0103 (4) | −0.0013 (4) | −0.0029 (4) |
| C15 | 0.0412 (6) | 0.0179 (4) | 0.0219 (4) | −0.0010 (4) | 0.0004 (4) | 0.0022 (3) |
| C16 | 0.0281 (5) | 0.0200 (5) | 0.0230 (4) | −0.0040 (4) | −0.0017 (4) | 0.0036 (3) |
| C17 | 0.0330 (5) | 0.0279 (5) | 0.0338 (5) | −0.0085 (4) | 0.0005 (4) | 0.0108 (4) |
| C18 | 0.0250 (5) | 0.0423 (7) | 0.0383 (6) | −0.0051 (4) | 0.0060 (4) | 0.0166 (5) |
| C19 | 0.0203 (4) | 0.0365 (6) | 0.0304 (5) | 0.0028 (4) | 0.0040 (4) | 0.0096 (4) |
| C20 | 0.0183 (4) | 0.0236 (5) | 0.0220 (4) | 0.0000 (3) | −0.0007 (3) | 0.0037 (3) |
| C21 | 0.0180 (4) | 0.0229 (5) | 0.0229 (4) | 0.0024 (3) | 0.0001 (3) | 0.0015 (3) |
| C22 | 0.0510 (7) | 0.0238 (5) | 0.0287 (5) | 0.0041 (5) | 0.0082 (5) | 0.0031 (4) |
| C23 | 0.0808 (10) | 0.0273 (6) | 0.0419 (7) | −0.0084 (6) | 0.0309 (7) | −0.0045 (5) |
| C24 | 0.0320 (5) | 0.0221 (5) | 0.0288 (5) | 0.0063 (4) | 0.0056 (4) | 0.0017 (4) |
| C25 | 0.0420 (6) | 0.0298 (6) | 0.0350 (6) | 0.0093 (5) | 0.0095 (5) | −0.0033 (4) |
| O1—C1 | 1.2064 (12) | C8—C9 | 1.5063 (15) |
| O2—C1 | 1.3289 (12) | C9—C10 | 1.3898 (14) |
| O2—C22 | 1.4603 (13) | C10—C11 | 1.3825 (18) |
| O3—C7 | 1.2100 (13) | C10—H10 | 0.9500 |
| O4—C8 | 1.2109 (13) | C11—C12 | 1.3854 (19) |
| O5—C14 | 1.2123 (13) | C11—H11 | 0.9500 |
| O6—C15 | 1.2131 (13) | C12—C13 | 1.3930 (15) |
| O7—C21 | 1.2034 (12) | C12—H12 | 0.9500 |
| O8—C21 | 1.3434 (12) | C13—C14 | 1.5052 (16) |
| O8—C24 | 1.4671 (12) | C15—C16 | 1.5068 (15) |
| N1—C2 | 1.3382 (13) | C16—C17 | 1.3880 (15) |
| N1—C6 | 1.3401 (13) | C17—C18 | 1.3809 (17) |
| N2—C7 | 1.3760 (13) | C17—H17 | 0.9500 |
| N2—C8 | 1.3809 (13) | C18—C19 | 1.3893 (16) |
| N2—H2 | 0.878 (15) | C18—H18 | 0.9500 |
| N3—C13 | 1.3348 (13) | C19—C20 | 1.3924 (14) |
| N3—C9 | 1.3354 (13) | C19—H19 | 0.9500 |
| N4—C15 | 1.3732 (14) | C20—C21 | 1.5057 (13) |
| N4—C14 | 1.3796 (14) | C22—C23 | 1.4949 (18) |
| N4—H4 | 0.885 (14) | C22—H22A | 0.9900 |
| N5—C16 | 1.3364 (12) | C22—H22B | 0.9900 |
| N5—C20 | 1.3384 (13) | C23—H23A | 0.9800 |
| C1—C2 | 1.5064 (14) | C23—H23B | 0.9800 |
| C2—C3 | 1.3979 (13) | C23—H23C | 0.9800 |
| C3—C4 | 1.3882 (15) | C24—C25 | 1.5064 (14) |
| C3—H3 | 0.9500 | C24—H24A | 0.9900 |
| C4—C5 | 1.3859 (15) | C24—H24B | 0.9900 |
| C4—H4A | 0.9500 | C25—H25A | 0.9800 |
| C5—C6 | 1.3895 (14) | C25—H25B | 0.9800 |
| C5—H5 | 0.9500 | C25—H25C | 0.9800 |
| C6—C7 | 1.5086 (14) | ||
| C1—O2—C22 | 116.47 (8) | C12—C13—C14 | 122.10 (10) |
| C21—O8—C24 | 114.60 (8) | O5—C14—N4 | 125.50 (11) |
| C2—N1—C6 | 117.56 (8) | O5—C14—C13 | 123.18 (10) |
| C7—N2—C8 | 129.30 (9) | N4—C14—C13 | 111.32 (8) |
| C7—N2—H2 | 114.2 (9) | O6—C15—N4 | 125.43 (11) |
| C8—N2—H2 | 116.3 (9) | O6—C15—C16 | 122.08 (10) |
| C13—N3—C9 | 118.83 (9) | N4—C15—C16 | 112.49 (8) |
| C15—N4—C14 | 129.10 (9) | N5—C16—C17 | 123.57 (10) |
| C15—N4—H4 | 115.0 (9) | N5—C16—C15 | 116.50 (9) |
| C14—N4—H4 | 115.7 (9) | C17—C16—C15 | 119.90 (9) |
| C16—N5—C20 | 117.56 (9) | C18—C17—C16 | 118.41 (10) |
| O1—C1—O2 | 125.14 (10) | C18—C17—H17 | 120.8 |
| O1—C1—C2 | 124.11 (9) | C16—C17—H17 | 120.8 |
| O2—C1—C2 | 110.75 (8) | C17—C18—C19 | 118.91 (10) |
| N1—C2—C3 | 122.96 (9) | C17—C18—H18 | 120.5 |
| N1—C2—C1 | 114.99 (8) | C19—C18—H18 | 120.5 |
| C3—C2—C1 | 122.04 (9) | C18—C19—C20 | 118.59 (10) |
| C4—C3—C2 | 118.48 (10) | C18—C19—H19 | 120.7 |
| C4—C3—H3 | 120.8 | C20—C19—H19 | 120.7 |
| C2—C3—H3 | 120.8 | N5—C20—C19 | 122.90 (9) |
| C5—C4—C3 | 119.04 (9) | N5—C20—C21 | 114.16 (8) |
| C5—C4—H4A | 120.5 | C19—C20—C21 | 122.92 (9) |
| C3—C4—H4A | 120.5 | O7—C21—O8 | 124.66 (9) |
| C4—C5—C6 | 118.31 (10) | O7—C21—C20 | 123.41 (9) |
| C4—C5—H5 | 120.8 | O8—C21—C20 | 111.94 (8) |
| C6—C5—H5 | 120.8 | O2—C22—C23 | 106.44 (9) |
| N1—C6—C5 | 123.57 (9) | O2—C22—H22A | 110.4 |
| N1—C6—C7 | 116.89 (8) | C23—C22—H22A | 110.4 |
| C5—C6—C7 | 119.53 (9) | O2—C22—H22B | 110.4 |
| O3—C7—N2 | 125.58 (10) | C23—C22—H22B | 110.4 |
| O3—C7—C6 | 122.35 (9) | H22A—C22—H22B | 108.6 |
| N2—C7—C6 | 112.06 (8) | C22—C23—H23A | 109.5 |
| O4—C8—N2 | 126.13 (10) | C22—C23—H23B | 109.5 |
| O4—C8—C9 | 122.81 (9) | H23A—C23—H23B | 109.5 |
| N2—C8—C9 | 111.02 (8) | C22—C23—H23C | 109.5 |
| N3—C9—C10 | 122.87 (10) | H23A—C23—H23C | 109.5 |
| N3—C9—C8 | 115.64 (8) | H23B—C23—H23C | 109.5 |
| C10—C9—C8 | 121.45 (10) | O8—C24—C25 | 108.13 (8) |
| C11—C10—C9 | 117.80 (11) | O8—C24—H24A | 110.1 |
| C11—C10—H10 | 121.1 | C25—C24—H24A | 110.1 |
| C9—C10—H10 | 121.1 | O8—C24—H24B | 110.1 |
| C10—C11—C12 | 120.02 (10) | C25—C24—H24B | 110.1 |
| C10—C11—H11 | 120.0 | H24A—C24—H24B | 108.4 |
| C12—C11—H11 | 120.0 | C24—C25—H25A | 109.5 |
| C11—C12—C13 | 118.10 (11) | C24—C25—H25B | 109.5 |
| C11—C12—H12 | 121.0 | H25A—C25—H25B | 109.5 |
| C13—C12—H12 | 121.0 | C24—C25—H25C | 109.5 |
| N3—C13—C12 | 122.34 (11) | H25A—C25—H25C | 109.5 |
| N3—C13—C14 | 115.55 (9) | H25B—C25—H25C | 109.5 |
| C22—O2—C1—O1 | −3.25 (15) | C9—N3—C13—C12 | −0.98 (14) |
| C22—O2—C1—C2 | 177.85 (8) | C9—N3—C13—C14 | 178.44 (8) |
| C6—N1—C2—C3 | 0.73 (13) | C11—C12—C13—N3 | 1.89 (16) |
| C6—N1—C2—C1 | −179.54 (8) | C11—C12—C13—C14 | −177.48 (10) |
| O1—C1—C2—N1 | −15.36 (14) | C15—N4—C14—O5 | −0.58 (18) |
| O2—C1—C2—N1 | 163.55 (8) | C15—N4—C14—C13 | 179.72 (9) |
| O1—C1—C2—C3 | 164.37 (10) | N3—C13—C14—O5 | 162.22 (10) |
| O2—C1—C2—C3 | −16.71 (12) | C12—C13—C14—O5 | −18.36 (16) |
| N1—C2—C3—C4 | 1.73 (14) | N3—C13—C14—N4 | −18.07 (12) |
| C1—C2—C3—C4 | −177.98 (8) | C12—C13—C14—N4 | 161.35 (9) |
| C2—C3—C4—C5 | −2.40 (14) | C14—N4—C15—O6 | 3.77 (18) |
| C3—C4—C5—C6 | 0.72 (14) | C14—N4—C15—C16 | −175.83 (9) |
| C2—N1—C6—C5 | −2.58 (14) | C20—N5—C16—C17 | −2.57 (14) |
| C2—N1—C6—C7 | 176.59 (8) | C20—N5—C16—C15 | 175.38 (8) |
| C4—C5—C6—N1 | 1.87 (15) | O6—C15—C16—N5 | 178.10 (10) |
| C4—C5—C6—C7 | −177.27 (9) | N4—C15—C16—N5 | −2.29 (12) |
| C8—N2—C7—O3 | −8.40 (18) | O6—C15—C16—C17 | −3.88 (15) |
| C8—N2—C7—C6 | 170.93 (9) | N4—C15—C16—C17 | 175.74 (9) |
| N1—C6—C7—O3 | 178.12 (10) | N5—C16—C17—C18 | 2.05 (16) |
| C5—C6—C7—O3 | −2.68 (15) | C15—C16—C17—C18 | −175.83 (10) |
| N1—C6—C7—N2 | −1.24 (12) | C16—C17—C18—C19 | 0.37 (16) |
| C5—C6—C7—N2 | 177.96 (9) | C17—C18—C19—C20 | −2.07 (16) |
| C7—N2—C8—O4 | 4.13 (18) | C16—N5—C20—C19 | 0.70 (14) |
| C7—N2—C8—C9 | −173.76 (9) | C16—N5—C20—C21 | 179.34 (8) |
| C13—N3—C9—C10 | −0.73 (14) | C18—C19—C20—N5 | 1.58 (15) |
| C13—N3—C9—C8 | 177.19 (8) | C18—C19—C20—C21 | −176.94 (9) |
| O4—C8—C9—N3 | 167.30 (9) | C24—O8—C21—O7 | −1.92 (13) |
| N2—C8—C9—N3 | −14.72 (12) | C24—O8—C21—C20 | 178.12 (8) |
| O4—C8—C9—C10 | −14.75 (15) | N5—C20—C21—O7 | −19.00 (13) |
| N2—C8—C9—C10 | 163.23 (9) | C19—C20—C21—O7 | 159.64 (10) |
| N3—C9—C10—C11 | 1.43 (15) | N5—C20—C21—O8 | 160.96 (8) |
| C8—C9—C10—C11 | −176.37 (10) | C19—C20—C21—O8 | −20.40 (13) |
| C9—C10—C11—C12 | −0.44 (17) | C1—O2—C22—C23 | 170.48 (10) |
| C10—C11—C12—C13 | −1.12 (17) | C21—O8—C24—C25 | 168.94 (8) |
| D—H···A | D—H | H···A | D···A | 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) |
| D—H···A | D—H | H···A | D···A | 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) |
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.
Huc, I. (2004). Eur. J. Org. Chem. pp. 17-29.
Li, X., Zhan, C., Wang, Y. & Yao, J. (2008). Chem. Commun. pp. 2444–2446.
Rigaku (1999). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
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).