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Acta Crystallogr Sect E Struct Rep Online. Apr 1, 2012; 68(Pt 4): o1272.
Published online Mar 31, 2012. doi:  10.1107/S1600536812013104
PMCID: PMC3344196
N-Cyclo­hexyl-N-{[3-(4,6-dimeth­oxy­pyrimidin-2-yl­oxy)pyridin-2-yl]meth­yl}4,6-dimeth­oxy­pyrimidin-2-amine
De-Cai Wang,a* Yu-Jing Wang,a Jun-Song Song,a Ping Wei,a and Ping-Kai Ou-yanga
aState Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People’s Republic of China
Correspondence e-mail: dc_wang/at/hotmail.com
Received March 20, 2012; Accepted March 26, 2012.
In the title compound, C24H30N6O5, the cyclo­hexyl ring adopts a chair conformation, while the remainder of the mol­ecule adopts a U-shape. The dihedral angles between the pyridine ring and the pendant pyrimidine rings are 69.04 (12) and 75.99 (9)°. The two pyrimidine rings, however, are nearly parallel to one another, with a dihedral angle of 8.56 (15)° between them. They are also involved in an intra­molecular π–π stacking inter­action with a distance of 3.6627 (18) Å between the ring centroids. In the crystal, C—H(...)O contacts link the mol­ecules into chains along the b axis.
Related literature  
For the synthesis and applications of the title compound, see: Yang & Lu (2010 [triangle]).
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Object name is e-68-o1272-scheme1.jpg Object name is e-68-o1272-scheme1.jpg
Crystal data  
  • C24H30N6O5
  • M r = 482.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o1272-efi1.jpg
  • a = 7.0260 (14) Å
  • b = 10.624 (2) Å
  • c = 17.084 (3) Å
  • α = 72.95 (3)°
  • β = 84.18 (3)°
  • γ = 79.56 (3)°
  • V = 1197.4 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm
Data collection  
  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.972, T max = 0.991
  • 4410 measured reflections
  • 4410 independent reflections
  • 2478 reflections with I > 2σ(I)
  • R int = 0.000
  • 3 standard reflections every 200 reflections intensity decay: 1%
Refinement  
  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.178
  • S = 1.00
  • 4410 reflections
  • 316 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.21 e Å−3
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013104/sj5221sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013104/sj5221Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812013104/sj5221Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The work was supported by the Center for Testing and Analysis, Nanjing University.
supplementary crystallographic information
Comment
The title compound is an important organic intermediate for the synthesis of pyrimidine-oxy-N-aryl benzyl amine derivatives, important compounds for use as new pesticides Yang & Lu (2010). In the process of synthesizing one such derivative, we obtained crystals of the intermediate and we report its crystal structure herein.
As shown in Fig.1, the cyclohexyl ring(C19—C24) adopts a chair conformation, while the remainder of the molecule is U shaped. The dihedral angles between the central pyridyl ring(C1—C5/N1) and the pendant pyrimidine rings (C6—C9/N2/N3 and C13—C16/N5/N6) are 69.04 (12) and 75.99 (9)°, respectively. The the two pyrimidine rings are nearly parallel to each other, with a dihedral angle of 8.56 (15)° between them. An intramolecular π-π stacking interaction also occurs with a distance of 3.6627 (18)Å between the (C6—C9/N2/N3) and (C13—C16/N5/N6) ring centroids. In the crystal, molecules are linked by weak C18—H18B···O hydrogen-bonds forming chains along b.
Experimental
The title compound was synthesized according to a published procedure (Yang & Lu, 2010). The product (0.3 g) was crystallized in methanol (15ml) at room temperature to give colorless crystals that were used for data collection.
Refinement
All H atoms were placed in calculated positions and treated as riding: C—H = 0.93 and 0.96 Å for CH and CH3 H atoms, respectively, with Uiso(H) = k × Ueq(C), where k = 1.5 for CH3 H-atoms and k = 1.2 for all other H-atoms.
Figures
Fig. 1.
Fig. 1.
The structure of the title compound, showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids.
Crystal data
C24H30N6O5Z = 2
Mr = 482.54F(000) = 512
Triclinic, P1Dx = 1.338 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0260 (14) ÅCell parameters from 25 reflections
b = 10.624 (2) Åθ = 9–13°
c = 17.084 (3) ŵ = 0.10 mm1
α = 72.95 (3)°T = 293 K
β = 84.18 (3)°Block, white
γ = 79.56 (3)°0.30 × 0.20 × 0.10 mm
V = 1197.4 (4) Å3
Data collection
Enraf–Nonius CAD-4 diffractometer2478 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 25.4°, θmin = 1.3°
ω/2θ scansh = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −12→12
Tmin = 0.972, Tmax = 0.991l = 0→20
4410 measured reflections3 standard reflections every 200 reflections
4410 independent reflections intensity decay: 1%
Refinement
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.088P)2] where P = (Fo2 + 2Fc2)/3
4410 reflections(Δ/σ)max < 0.001
316 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.21 e Å3
Special details
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)
xyzUiso*/Ueq
O1−0.5779 (3)−0.4010 (2)0.30512 (12)0.0540 (6)
N1−0.2211 (4)−0.6995 (3)0.32680 (17)0.0611 (8)
C1−0.5799 (5)−0.5959 (3)0.2625 (2)0.0603 (9)
H1B−0.7015−0.56080.24160.072*
N2−0.6650 (3)−0.1812 (2)0.25672 (15)0.0465 (6)
N3−0.5486 (4)−0.3123 (2)0.16500 (15)0.0478 (6)
O2−0.5286 (3)−0.2115 (2)0.02694 (13)0.0630 (6)
C2−0.4927 (6)−0.7205 (4)0.2608 (2)0.0678 (10)
H2B−0.5505−0.77110.23680.081*
O3−0.7485 (3)0.0450 (2)0.20679 (14)0.0602 (6)
C3−0.3169 (6)−0.7692 (3)0.2957 (2)0.0681 (10)
H3A−0.2613−0.85640.29760.082*
O40.0337 (3)−0.4581 (2)0.08476 (13)0.0645 (7)
N4−0.1984 (4)−0.3603 (2)0.32456 (14)0.0485 (7)
C4−0.3046 (5)−0.5749 (3)0.32542 (18)0.0490 (8)
O5−0.1294 (3)−0.0173 (2)0.09128 (13)0.0605 (6)
N5−0.0728 (3)−0.4126 (2)0.20658 (14)0.0447 (6)
C5−0.4850 (5)−0.5237 (3)0.29541 (18)0.0488 (8)
N6−0.1554 (3)−0.1847 (2)0.21032 (14)0.0451 (6)
C6−0.5969 (4)−0.2925 (3)0.23752 (18)0.0451 (7)
C7−0.5704 (4)−0.2005 (3)0.10297 (19)0.0484 (8)
C8−0.6346 (5)−0.0770 (3)0.1132 (2)0.0547 (8)
H8A−0.6451−0.00010.06930.066*
C9−0.6827 (4)−0.0735 (3)0.1924 (2)0.0486 (8)
C10−0.4772 (6)−0.3424 (4)0.0165 (2)0.0772 (11)
H10A−0.4518−0.3359−0.04070.116*
H10B−0.5820−0.39170.03750.116*
H10C−0.3633−0.38750.04580.116*
C11−0.8112 (6)0.0430 (3)0.2890 (2)0.0740 (11)
H11A−0.85580.13260.29180.111*
H11B−0.70500.00340.32410.111*
H11C−0.9149−0.00830.30650.111*
C12−0.1847 (5)−0.5041 (3)0.36202 (19)0.0537 (8)
H12A−0.2232−0.51940.41980.064*
H12B−0.0500−0.54450.35830.064*
C13−0.1381 (4)−0.3174 (3)0.24449 (17)0.0421 (7)
C14−0.0298 (4)−0.3675 (3)0.12722 (19)0.0483 (8)
C15−0.0444 (5)−0.2355 (3)0.08470 (19)0.0536 (8)
H15A−0.0130−0.20690.02880.064*
C16−0.1090 (4)−0.1485 (3)0.13068 (18)0.0462 (8)
C170.0071 (6)−0.5926 (4)0.1224 (2)0.0745 (11)
H17A0.0587−0.64580.08600.112*
H17B−0.1286−0.59640.13380.112*
H17C0.0734−0.62630.17260.112*
C18−0.2060 (5)0.0734 (3)0.1364 (2)0.0599 (9)
H18A−0.21290.16280.10120.090*
H18B−0.12390.06150.18050.090*
H18C−0.33360.05770.15840.090*
C19−0.2291 (5)−0.2710 (3)0.37820 (17)0.0505 (8)
H19A−0.2527−0.17980.34190.061*
C20−0.0472 (5)−0.2818 (3)0.4213 (2)0.0613 (9)
H20A0.0598−0.26490.38110.074*
H20B−0.0156−0.37150.45720.074*
C21−0.0747 (6)−0.1815 (4)0.4717 (2)0.0773 (12)
H21A0.0391−0.19590.50280.093*
H21B−0.0871−0.09180.43480.093*
C22−0.2499 (6)−0.1934 (4)0.5293 (2)0.0775 (12)
H22A−0.2686−0.12290.55600.093*
H22B−0.2298−0.27820.57130.093*
C232−0.4279 (6)−0.1842 (4)0.4849 (2)0.0811 (12)
H23A−0.4566−0.09560.44750.097*
H23B−0.5371−0.19800.52430.097*
C24−0.4025 (5)−0.2862 (4)0.4373 (2)0.0696 (11)
H24A−0.3858−0.37520.47500.084*
H24B−0.5176−0.27470.40750.084*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
O10.0638 (15)0.0462 (13)0.0439 (12)0.0004 (10)0.0010 (11)−0.0068 (10)
N10.078 (2)0.0425 (17)0.0560 (17)0.0019 (14)0.0017 (15)−0.0122 (13)
C10.058 (2)0.059 (2)0.065 (2)−0.0150 (18)−0.0010 (18)−0.0151 (18)
N20.0416 (15)0.0436 (15)0.0524 (16)−0.0058 (12)−0.0014 (12)−0.0117 (13)
N30.0482 (16)0.0485 (16)0.0466 (15)−0.0090 (12)−0.0040 (12)−0.0117 (13)
O20.0733 (17)0.0669 (16)0.0448 (13)−0.0085 (12)−0.0014 (11)−0.0116 (11)
C20.079 (3)0.054 (2)0.075 (3)−0.018 (2)0.004 (2)−0.0232 (19)
O30.0629 (15)0.0441 (14)0.0702 (16)−0.0059 (11)0.0003 (12)−0.0137 (11)
C30.093 (3)0.041 (2)0.069 (2)−0.007 (2)0.004 (2)−0.0182 (18)
O40.0783 (17)0.0678 (16)0.0531 (14)−0.0184 (13)0.0168 (12)−0.0282 (12)
N40.0631 (18)0.0460 (15)0.0341 (13)−0.0075 (12)0.0016 (12)−0.0098 (11)
C40.060 (2)0.0434 (19)0.0406 (17)−0.0065 (16)0.0054 (15)−0.0100 (14)
O50.0741 (16)0.0578 (15)0.0450 (12)−0.0160 (12)0.0096 (12)−0.0080 (11)
N50.0443 (15)0.0508 (16)0.0396 (14)−0.0043 (12)−0.0007 (11)−0.0159 (12)
C50.058 (2)0.0387 (18)0.0433 (17)−0.0031 (15)0.0043 (16)−0.0072 (14)
N60.0442 (16)0.0504 (16)0.0394 (14)−0.0098 (12)−0.0010 (12)−0.0097 (12)
C60.0408 (18)0.0456 (19)0.0443 (18)−0.0062 (14)−0.0032 (14)−0.0057 (14)
C70.0439 (19)0.057 (2)0.0427 (18)−0.0137 (15)−0.0047 (14)−0.0083 (16)
C80.055 (2)0.047 (2)0.056 (2)−0.0108 (16)−0.0042 (17)−0.0024 (16)
C90.0404 (18)0.0412 (19)0.064 (2)−0.0068 (14)−0.0050 (16)−0.0129 (16)
C100.084 (3)0.087 (3)0.061 (2)−0.001 (2)0.001 (2)−0.032 (2)
C110.086 (3)0.054 (2)0.080 (3)−0.0045 (19)0.009 (2)−0.024 (2)
C120.064 (2)0.050 (2)0.0414 (17)−0.0009 (16)−0.0050 (16)−0.0083 (15)
C130.0374 (17)0.056 (2)0.0339 (16)−0.0076 (14)−0.0015 (13)−0.0146 (14)
C140.0407 (19)0.065 (2)0.0447 (18)−0.0107 (15)0.0062 (14)−0.0256 (17)
C150.060 (2)0.064 (2)0.0394 (17)−0.0178 (17)0.0090 (16)−0.0170 (16)
C160.0400 (18)0.054 (2)0.0431 (18)−0.0133 (15)0.0021 (14)−0.0096 (15)
C170.096 (3)0.063 (3)0.071 (3)−0.014 (2)0.005 (2)−0.032 (2)
C180.069 (2)0.055 (2)0.056 (2)−0.0132 (17)−0.0010 (18)−0.0146 (17)
C190.069 (2)0.0458 (19)0.0331 (16)−0.0043 (16)0.0013 (15)−0.0098 (14)
C200.065 (2)0.070 (2)0.053 (2)−0.0135 (18)0.0004 (18)−0.0237 (18)
C210.099 (3)0.084 (3)0.063 (2)−0.029 (2)−0.001 (2)−0.035 (2)
C220.108 (3)0.080 (3)0.051 (2)−0.010 (2)−0.001 (2)−0.032 (2)
C2320.088 (3)0.099 (3)0.055 (2)0.008 (2)0.005 (2)−0.036 (2)
C240.062 (2)0.097 (3)0.054 (2)−0.007 (2)0.0021 (18)−0.033 (2)
Geometric parameters (Å, º)
O1—C61.370 (3)C10—H10A0.9600
O1—C51.396 (3)C10—H10B0.9600
N1—C31.331 (4)C10—H10C0.9600
N1—C41.342 (4)C11—H11A0.9600
C1—C21.361 (4)C11—H11B0.9600
C1—C51.366 (4)C11—H11C0.9600
C1—H1B0.9300C12—H12A0.9700
N2—C61.314 (4)C12—H12B0.9700
N2—C91.331 (4)C14—C151.368 (4)
N3—C61.318 (4)C15—C161.371 (4)
N3—C71.337 (4)C15—H15A0.9300
O2—C71.337 (4)C17—H17A0.9600
O2—C101.431 (4)C17—H17B0.9600
C2—C31.373 (5)C17—H17C0.9600
C2—H2B0.9300C18—H18A0.9600
O3—C91.344 (3)C18—H18B0.9600
O3—C111.424 (4)C18—H18C0.9600
C3—H3A0.9300C19—C241.502 (4)
O4—C141.357 (3)C19—C201.509 (4)
O4—C171.422 (4)C19—H19A0.9800
N4—C131.358 (4)C20—C211.531 (4)
N4—C121.462 (4)C20—H20A0.9700
N4—C191.478 (4)C20—H20B0.9700
C4—C51.372 (4)C21—C221.496 (5)
C4—C121.509 (4)C21—H21A0.9700
O5—C161.346 (3)C21—H21B0.9700
O5—C181.405 (4)C22—C2321.501 (5)
N5—C141.322 (4)C22—H22A0.9700
N5—C131.344 (4)C22—H22B0.9700
N6—C161.324 (4)C232—C241.511 (5)
N6—C131.347 (4)C232—H23A0.9700
C7—C81.363 (4)C232—H23B0.9700
C8—C91.370 (4)C24—H24A0.9700
C8—H8A0.9300C24—H24B0.9700
C6—O1—C5118.7 (2)N5—C13—N4116.2 (3)
C3—N1—C4117.5 (3)N6—C13—N4117.2 (3)
C2—C1—C5118.6 (3)N5—C14—O4117.9 (3)
C2—C1—H1B120.7N5—C14—C15124.6 (3)
C5—C1—H1B120.7O4—C14—C15117.5 (3)
C6—N2—C9113.8 (3)C14—C15—C16115.0 (3)
C6—N3—C7113.6 (3)C14—C15—H15A122.5
C7—O2—C10118.1 (3)C16—C15—H15A122.5
C1—C2—C3118.0 (3)N6—C16—O5118.2 (3)
C1—C2—H2B121.0N6—C16—C15124.5 (3)
C3—C2—H2B121.0O5—C16—C15117.2 (3)
C9—O3—C11116.9 (3)O4—C17—H17A109.5
N1—C3—C2124.1 (3)O4—C17—H17B109.5
N1—C3—H3A118.0H17A—C17—H17B109.5
C2—C3—H3A118.0O4—C17—H17C109.5
C14—O4—C17118.1 (3)H17A—C17—H17C109.5
C13—N4—C12117.9 (2)H17B—C17—H17C109.5
C13—N4—C19121.4 (2)O5—C18—H18A109.5
C12—N4—C19118.9 (2)O5—C18—H18B109.5
N1—C4—C5120.9 (3)H18A—C18—H18B109.5
N1—C4—C12113.4 (3)O5—C18—H18C109.5
C5—C4—C12125.7 (3)H18A—C18—H18C109.5
C16—O5—C18118.1 (2)H18B—C18—H18C109.5
C14—N5—C13114.8 (3)N4—C19—C24114.9 (3)
C1—C5—C4120.8 (3)N4—C19—C20110.8 (3)
C1—C5—O1119.9 (3)C24—C19—C20111.6 (3)
C4—C5—O1119.0 (3)N4—C19—H19A106.3
C16—N6—C13114.6 (3)C24—C19—H19A106.3
N2—C6—N3129.7 (3)C20—C19—H19A106.3
N2—C6—O1112.3 (3)C19—C20—C21110.6 (3)
N3—C6—O1118.0 (3)C19—C20—H20A109.5
O2—C7—N3117.7 (3)C21—C20—H20A109.5
O2—C7—C8118.7 (3)C19—C20—H20B109.5
N3—C7—C8123.6 (3)C21—C20—H20B109.5
C7—C8—C9115.6 (3)H20A—C20—H20B108.1
C7—C8—H8A122.2C22—C21—C20112.2 (3)
C9—C8—H8A122.2C22—C21—H21A109.2
N2—C9—O3117.6 (3)C20—C21—H21A109.2
N2—C9—C8123.7 (3)C22—C21—H21B109.2
O3—C9—C8118.7 (3)C20—C21—H21B109.2
O2—C10—H10A109.5H21A—C21—H21B107.9
O2—C10—H10B109.5C21—C22—C232111.3 (3)
H10A—C10—H10B109.5C21—C22—H22A109.4
O2—C10—H10C109.5C232—C22—H22A109.4
H10A—C10—H10C109.5C21—C22—H22B109.4
H10B—C10—H10C109.5C232—C22—H22B109.4
O3—C11—H11A109.5H22A—C22—H22B108.0
O3—C11—H11B109.5C22—C232—C24111.8 (3)
H11A—C11—H11B109.5C22—C232—H23A109.3
O3—C11—H11C109.5C24—C232—H23A109.3
H11A—C11—H11C109.5C22—C232—H23B109.3
H11B—C11—H11C109.5C24—C232—H23B109.3
N4—C12—C4115.9 (3)H23A—C232—H23B107.9
N4—C12—H12A108.3C19—C24—C232110.5 (3)
C4—C12—H12A108.3C19—C24—H24A109.6
N4—C12—H12B108.3C232—C24—H24A109.6
C4—C12—H12B108.3C19—C24—H24B109.6
H12A—C12—H12B107.4C232—C24—H24B109.6
N5—C13—N6126.5 (3)H24A—C24—H24B108.1
C5—C1—C2—C32.7 (5)C5—C4—C12—N4−35.9 (4)
C4—N1—C3—C21.5 (5)C14—N5—C13—N6−2.8 (4)
C1—C2—C3—N1−4.0 (6)C14—N5—C13—N4174.9 (3)
C3—N1—C4—C52.1 (4)C16—N6—C13—N52.8 (4)
C3—N1—C4—C12−179.9 (3)C16—N6—C13—N4−174.9 (3)
C2—C1—C5—C40.7 (5)C12—N4—C13—N50.8 (4)
C2—C1—C5—O1−173.9 (3)C19—N4—C13—N5165.3 (3)
N1—C4—C5—C1−3.3 (5)C12—N4—C13—N6178.6 (2)
C12—C4—C5—C1179.1 (3)C19—N4—C13—N6−16.8 (4)
N1—C4—C5—O1171.4 (3)C13—N5—C14—O4−178.8 (2)
C12—C4—C5—O1−6.2 (5)C13—N5—C14—C151.3 (4)
C6—O1—C5—C1−76.2 (4)C17—O4—C14—N514.6 (4)
C6—O1—C5—C4109.0 (3)C17—O4—C14—C15−165.5 (3)
C9—N2—C6—N3−1.5 (5)N5—C14—C15—C160.0 (5)
C9—N2—C6—O1179.2 (2)O4—C14—C15—C16−179.9 (3)
C7—N3—C6—N21.3 (5)C13—N6—C16—O5177.5 (2)
C7—N3—C6—O1−179.4 (3)C13—N6—C16—C15−1.2 (4)
C5—O1—C6—N2−172.2 (3)C18—O5—C16—N6−2.4 (4)
C5—O1—C6—N38.4 (4)C18—O5—C16—C15176.4 (3)
C10—O2—C7—N34.5 (4)C14—C15—C16—N60.0 (5)
C10—O2—C7—C8−174.8 (3)C14—C15—C16—O5−178.8 (3)
C6—N3—C7—O2−178.6 (3)C13—N4—C19—C24140.8 (3)
C6—N3—C7—C80.6 (4)C12—N4—C19—C24−54.8 (4)
O2—C7—C8—C9177.3 (3)C13—N4—C19—C20−91.5 (3)
N3—C7—C8—C9−2.0 (5)C12—N4—C19—C2072.9 (3)
C6—N2—C9—O3−179.0 (2)N4—C19—C20—C21175.7 (3)
C6—N2—C9—C8−0.1 (4)C24—C19—C20—C21−54.9 (4)
C11—O3—C9—N2−5.9 (4)C19—C20—C21—C2253.5 (4)
C11—O3—C9—C8175.2 (3)C20—C21—C22—C232−53.7 (5)
C7—C8—C9—N21.7 (5)C21—C22—C232—C2455.3 (5)
C7—C8—C9—O3−179.5 (3)N4—C19—C24—C232−176.2 (3)
C13—N4—C12—C4−62.4 (4)C20—C19—C24—C23256.6 (4)
C19—N4—C12—C4132.7 (3)C22—C232—C24—C19−56.5 (4)
N1—C4—C12—N4146.3 (3)
Hydrogen-bond geometry (Å, º)
D—H···AD—HH···AD···AD—H···A
C18—H18B···O3i0.962.693.477 (4)140
Symmetry code: (i) x+1, y, z.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5221).
References
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  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yang, Z. M. & Lu, L. (2010). J. Label. Compd Radiopharm. 53, 192–197.
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