Abstract
The title compound, C24H27N3O4, also known as fenpyroximate, is a commercial acaricide. The benzene ring of the phenoxy group is approximately perpendicular to the pyrazole ring with a dihedral angle of 84.37 (11)°. The dihedral angle between the phenoxy and the benzoate benzene rings is 48.83 (8)°.
Related literature
For background to the design of bioactive molecules, see: Lewis et al. (1991 ▶) and for a related structure, see: Zou et al. (2006 ▶).
Experimental
Crystal data
C24H27N3O4
M r = 421.49
Triclinic,
a = 9.672 (3) Å
b = 9.908 (3) Å
c = 13.179 (3) Å
α = 72.487 (5)°
β = 71.614 (5)°
γ = 74.494 (4)°
V = 1122.0 (6) Å3
Z = 2
Mo Kα radiation
μ = 0.09 mm−1
T = 294 (2) K
0.32 × 0.24 × 0.20 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.972, T max = 0.983
5754 measured reflections
3941 independent reflections
2284 reflections with I > 2σ(I)
R int = 0.022
Refinement
R[F 2 > 2σ(F 2)] = 0.055
wR(F 2) = 0.175
S = 1.06
3941 reflections
284 parameters
H-atom parameters constrained
Δρmax = 0.36 e Å−3
Δρmin = −0.22 e Å−3
Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1999 ▶); software used to prepare material for publication: SHELXTL.
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680705427X/sj2396sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S160053680705427X/sj2396Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
This work was supported by the National Key Project for Basic Research (No. 20772067).
supplementary crystallographic information
Comment
Since biological activities are related to the conformation of molecules, study of the relationships between chemical structure and biological activity is important in the rational design of bioactive molecules (Lewis et al., 1991). The title compound, also known as Fenpyroximate, is a commercial acaricide. Details of its crystal structure may be helpful for the design of new acaricidal compounds and we report here the structure of the title compound (I), Fig. 1. In (I), the benzene ring (C1/C2/C3/C4/C5/C6) is approximately perpendicular to the pyrazole ring with a dihedral angle of 84.37 (11) ° between them. The dihedral angle between the benzoate benzene ring(C14/C15/C16/C17/C18/C19) and the pyrazole ring is 64.87 (11) °. This is different to the dihedral angle between the pyrimidine ring and the pyrazole ring in (E)-5(3,5-dimethylphenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde O-(2-chloropyrimidin-4-yl)oxime (Zou et al., 2006).
Experimental
Tert-butyl-(4-bromomethyl)benzoate(2.2 mmol), anhydrous potassium carbonate (4 mmol), and 1,3-dimethyl-5-phenoxy-1H-pyrazole-4- carbaldehyde oxime (2 mmol) were mixed in acetonitrile (40 ml) and refluxed for 5 h. The solvent was then evaporated in vacuo. The residue was recrystallized from ethanol and single crystals of (I) suitable for X-ray analysis were grown from ethyl acetate and petroleum ether at room temperature.
Refinement
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic 0.97 Å, Uiso = 1.2Ueq (C) for CH2 and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms.
Figures
Fig. 1.
View of the title compound with displacement ellipsoids drawn at the 30% probability level.
Crystal data
| C24H27N3O4 | Z = 2 |
| Mr = 421.49 | F000 = 448 |
| Triclinic, P1 | Dx = 1.248 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 9.672 (3) Å | Cell parameters from 1585 reflections |
| b = 9.908 (3) Å | θ = 2.2–22.6º |
| c = 13.179 (3) Å | µ = 0.09 mm−1 |
| α = 72.487 (5)º | T = 294 (2) K |
| β = 71.614 (5)º | Prism, colorless |
| γ = 74.494 (4)º | 0.32 × 0.24 × 0.20 mm |
| V = 1122.0 (6) Å3 |
Data collection
| Bruker SMART CCD area-detector diffractometer | 3941 independent reflections |
| Radiation source: fine-focus sealed tube | 2284 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.022 |
| T = 294(2) K | θmax = 25.0º |
| φ and ω scans | θmin = 1.7º |
| Absorption correction: multi-scan(SADABS; Bruker, 1999) | h = −11→11 |
| Tmin = 0.972, Tmax = 0.983 | k = −8→11 |
| 5754 measured reflections | l = −10→15 |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
| wR(F2) = 0.175 | w = 1/[σ2(Fo2) + (0.0841P)2 + 0.1856P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 3941 reflections | Δρmax = 0.36 e Å−3 |
| 284 parameters | Δρmin = −0.22 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
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)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.26628 (19) | 1.1772 (2) | −0.00386 (14) | 0.0554 (5) | |
| O2 | 0.3962 (2) | 0.6532 (2) | 0.19530 (16) | 0.0616 (6) | |
| O3 | 1.0760 (3) | 0.3688 (3) | 0.34012 (19) | 0.0934 (9) | |
| O4 | 0.9545 (2) | 0.2420 (2) | 0.49895 (15) | 0.0561 (5) | |
| N1 | 0.3522 (3) | 1.2674 (3) | 0.1062 (2) | 0.0559 (6) | |
| N2 | 0.4285 (3) | 1.2208 (3) | 0.1845 (2) | 0.0609 (7) | |
| N3 | 0.4010 (3) | 0.7806 (3) | 0.2206 (2) | 0.0542 (6) | |
| C1 | 0.1138 (3) | 1.1919 (3) | 0.0179 (2) | 0.0441 (7) | |
| C2 | 0.0642 (3) | 1.1915 (3) | −0.0686 (2) | 0.0601 (8) | |
| H2 | 0.1307 | 1.1812 | −0.1356 | 0.072* | |
| C3 | −0.0863 (4) | 1.2068 (4) | −0.0544 (3) | 0.0743 (10) | |
| H3 | −0.1213 | 1.2064 | −0.1124 | 0.089* | |
| C4 | −0.1839 (4) | 1.2223 (3) | 0.0431 (3) | 0.0673 (9) | |
| H4 | −0.2850 | 1.2318 | 0.0520 | 0.081* | |
| C5 | −0.1329 (3) | 1.2238 (3) | 0.1279 (3) | 0.0612 (8) | |
| H5 | −0.2000 | 1.2349 | 0.1945 | 0.073* | |
| C6 | 0.0167 (3) | 1.2090 (3) | 0.1166 (2) | 0.0545 (8) | |
| H6 | 0.0510 | 1.2106 | 0.1746 | 0.065* | |
| C7 | 0.3276 (3) | 1.1573 (3) | 0.0806 (2) | 0.0479 (7) | |
| C8 | 0.3863 (3) | 1.0308 (3) | 0.1450 (2) | 0.0456 (7) | |
| C9 | 0.4502 (3) | 1.0776 (3) | 0.2080 (2) | 0.0519 (7) | |
| C10 | 0.5368 (4) | 0.9888 (4) | 0.2888 (3) | 0.0734 (10) | |
| H10A | 0.5743 | 1.0507 | 0.3132 | 0.110* | |
| H10B | 0.6183 | 0.9235 | 0.2545 | 0.110* | |
| H10C | 0.4738 | 0.9348 | 0.3507 | 0.110* | |
| C11 | 0.3029 (4) | 1.4211 (3) | 0.0637 (3) | 0.0784 (10) | |
| H11A | 0.3730 | 1.4549 | −0.0036 | 0.118* | |
| H11B | 0.2959 | 1.4727 | 0.1168 | 0.118* | |
| H11C | 0.2074 | 1.4370 | 0.0499 | 0.118* | |
| C12 | 0.3833 (3) | 0.8883 (3) | 0.1411 (2) | 0.0493 (7) | |
| H12 | 0.3681 | 0.8747 | 0.0790 | 0.059* | |
| C13 | 0.3981 (3) | 0.5385 (3) | 0.2913 (3) | 0.0615 (8) | |
| H13A | 0.3680 | 0.4583 | 0.2816 | 0.074* | |
| H13B | 0.3258 | 0.5706 | 0.3536 | 0.074* | |
| C14 | 0.5472 (3) | 0.4862 (3) | 0.3174 (2) | 0.0499 (7) | |
| C15 | 0.5588 (3) | 0.3798 (3) | 0.4126 (3) | 0.0631 (9) | |
| H15 | 0.4754 | 0.3429 | 0.4580 | 0.076* | |
| C16 | 0.6917 (3) | 0.3281 (3) | 0.4406 (2) | 0.0569 (8) | |
| H16 | 0.6969 | 0.2582 | 0.5055 | 0.068* | |
| C17 | 0.8173 (3) | 0.3792 (3) | 0.3734 (2) | 0.0457 (7) | |
| C18 | 0.8060 (3) | 0.4847 (3) | 0.2779 (2) | 0.0536 (7) | |
| H18 | 0.8900 | 0.5200 | 0.2315 | 0.064* | |
| C19 | 0.6725 (3) | 0.5377 (3) | 0.2510 (2) | 0.0518 (7) | |
| H19 | 0.6667 | 0.6093 | 0.1872 | 0.062* | |
| C20 | 0.9636 (3) | 0.3290 (3) | 0.4004 (2) | 0.0532 (7) | |
| C21 | 1.0809 (3) | 0.1863 (3) | 0.5491 (2) | 0.0522 (7) | |
| C22 | 1.2093 (4) | 0.1033 (5) | 0.4795 (3) | 0.1094 (16) | |
| H22A | 1.1775 | 0.0273 | 0.4668 | 0.164* | |
| H22B | 1.2871 | 0.0626 | 0.5167 | 0.164* | |
| H22C | 1.2456 | 0.1668 | 0.4103 | 0.164* | |
| C23 | 1.0184 (5) | 0.0865 (5) | 0.6550 (3) | 0.1151 (17) | |
| H23A | 0.9339 | 0.1395 | 0.6979 | 0.173* | |
| H23B | 1.0927 | 0.0446 | 0.6955 | 0.173* | |
| H23C | 0.9886 | 0.0115 | 0.6394 | 0.173* | |
| C24 | 1.1218 (5) | 0.3089 (4) | 0.5687 (4) | 0.1043 (14) | |
| H24A | 1.1617 | 0.3702 | 0.4994 | 0.156* | |
| H24B | 1.1949 | 0.2726 | 0.6104 | 0.156* | |
| H24C | 1.0352 | 0.3630 | 0.6090 | 0.156* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0442 (11) | 0.0691 (14) | 0.0429 (11) | −0.0020 (9) | −0.0124 (9) | −0.0054 (9) |
| O2 | 0.0750 (14) | 0.0483 (12) | 0.0716 (14) | −0.0077 (10) | −0.0418 (11) | −0.0080 (10) |
| O3 | 0.0540 (14) | 0.124 (2) | 0.0669 (16) | −0.0101 (14) | −0.0133 (12) | 0.0198 (14) |
| O4 | 0.0515 (12) | 0.0629 (13) | 0.0494 (12) | −0.0120 (9) | −0.0224 (9) | 0.0041 (10) |
| N1 | 0.0533 (15) | 0.0509 (15) | 0.0583 (15) | −0.0045 (12) | −0.0181 (12) | −0.0063 (12) |
| N2 | 0.0529 (15) | 0.0655 (18) | 0.0656 (17) | −0.0076 (12) | −0.0213 (13) | −0.0145 (13) |
| N3 | 0.0561 (15) | 0.0490 (15) | 0.0595 (16) | −0.0021 (11) | −0.0254 (12) | −0.0114 (12) |
| C1 | 0.0431 (16) | 0.0375 (15) | 0.0456 (16) | −0.0048 (11) | −0.0137 (13) | −0.0010 (12) |
| C2 | 0.0605 (19) | 0.071 (2) | 0.0476 (18) | −0.0151 (16) | −0.0105 (15) | −0.0140 (15) |
| C3 | 0.068 (2) | 0.094 (3) | 0.071 (2) | −0.0225 (19) | −0.0294 (19) | −0.016 (2) |
| C4 | 0.0504 (19) | 0.066 (2) | 0.088 (3) | −0.0082 (15) | −0.0240 (19) | −0.0171 (18) |
| C5 | 0.0486 (18) | 0.065 (2) | 0.065 (2) | −0.0076 (15) | −0.0050 (15) | −0.0201 (16) |
| C6 | 0.0529 (18) | 0.0619 (19) | 0.0471 (18) | −0.0077 (14) | −0.0146 (14) | −0.0117 (14) |
| C7 | 0.0377 (15) | 0.0532 (18) | 0.0447 (16) | −0.0033 (13) | −0.0087 (13) | −0.0065 (13) |
| C8 | 0.0363 (14) | 0.0491 (17) | 0.0457 (16) | −0.0042 (12) | −0.0104 (12) | −0.0065 (13) |
| C9 | 0.0362 (15) | 0.061 (2) | 0.0538 (18) | −0.0045 (13) | −0.0124 (13) | −0.0102 (14) |
| C10 | 0.0582 (19) | 0.084 (2) | 0.081 (2) | −0.0019 (17) | −0.0388 (17) | −0.0120 (18) |
| C11 | 0.091 (3) | 0.051 (2) | 0.087 (3) | −0.0066 (17) | −0.030 (2) | −0.0051 (17) |
| C12 | 0.0393 (15) | 0.0579 (19) | 0.0472 (17) | −0.0026 (13) | −0.0161 (13) | −0.0079 (14) |
| C13 | 0.067 (2) | 0.0487 (18) | 0.074 (2) | −0.0127 (15) | −0.0381 (17) | 0.0007 (15) |
| C14 | 0.0603 (18) | 0.0389 (15) | 0.0568 (18) | −0.0069 (13) | −0.0279 (15) | −0.0091 (13) |
| C15 | 0.0567 (19) | 0.0589 (19) | 0.067 (2) | −0.0178 (15) | −0.0245 (16) | 0.0097 (15) |
| C16 | 0.0611 (19) | 0.0506 (18) | 0.0541 (18) | −0.0128 (14) | −0.0244 (15) | 0.0067 (14) |
| C17 | 0.0513 (17) | 0.0414 (15) | 0.0439 (16) | −0.0029 (12) | −0.0165 (13) | −0.0102 (12) |
| C18 | 0.0520 (17) | 0.0590 (19) | 0.0445 (17) | −0.0078 (14) | −0.0138 (14) | −0.0055 (14) |
| C19 | 0.0616 (19) | 0.0490 (17) | 0.0413 (16) | −0.0051 (14) | −0.0195 (14) | −0.0034 (13) |
| C20 | 0.0542 (19) | 0.0549 (18) | 0.0452 (18) | −0.0018 (14) | −0.0160 (15) | −0.0083 (14) |
| C21 | 0.0502 (16) | 0.0573 (18) | 0.0492 (17) | −0.0058 (14) | −0.0231 (14) | −0.0055 (14) |
| C22 | 0.105 (3) | 0.112 (3) | 0.106 (3) | 0.049 (3) | −0.059 (3) | −0.046 (3) |
| C23 | 0.089 (3) | 0.156 (4) | 0.080 (3) | −0.039 (3) | −0.048 (2) | 0.042 (3) |
| C24 | 0.122 (3) | 0.080 (3) | 0.140 (4) | −0.012 (2) | −0.085 (3) | −0.021 (3) |
Geometric parameters (Å, °)
| O1—C7 | 1.360 (3) | C11—H11A | 0.9600 |
| O1—C1 | 1.386 (3) | C11—H11B | 0.9600 |
| O2—N3 | 1.414 (3) | C11—H11C | 0.9600 |
| O2—C13 | 1.425 (3) | C12—H12 | 0.9300 |
| O3—C20 | 1.210 (3) | C13—C14 | 1.507 (4) |
| O4—C20 | 1.316 (3) | C13—H13A | 0.9700 |
| O4—C21 | 1.471 (3) | C13—H13B | 0.9700 |
| N1—C7 | 1.332 (4) | C14—C19 | 1.373 (4) |
| N1—N2 | 1.355 (3) | C14—C15 | 1.388 (4) |
| N1—C11 | 1.458 (4) | C15—C16 | 1.373 (4) |
| N2—C9 | 1.331 (4) | C15—H15 | 0.9300 |
| N3—C12 | 1.268 (3) | C16—C17 | 1.377 (4) |
| C1—C2 | 1.370 (4) | C16—H16 | 0.9300 |
| C1—C6 | 1.371 (4) | C17—C18 | 1.386 (4) |
| C2—C3 | 1.380 (4) | C17—C20 | 1.487 (4) |
| C2—H2 | 0.9300 | C18—C19 | 1.373 (4) |
| C3—C4 | 1.358 (4) | C18—H18 | 0.9300 |
| C3—H3 | 0.9300 | C19—H19 | 0.9300 |
| C4—C5 | 1.361 (4) | C21—C24 | 1.487 (5) |
| C4—H4 | 0.9300 | C21—C23 | 1.499 (4) |
| C5—C6 | 1.379 (4) | C21—C22 | 1.500 (5) |
| C5—H5 | 0.9300 | C22—H22A | 0.9600 |
| C6—H6 | 0.9300 | C22—H22B | 0.9600 |
| C7—C8 | 1.377 (4) | C22—H22C | 0.9600 |
| C8—C9 | 1.413 (4) | C23—H23A | 0.9600 |
| C8—C12 | 1.436 (4) | C23—H23B | 0.9600 |
| C9—C10 | 1.489 (4) | C23—H23C | 0.9600 |
| C10—H10A | 0.9600 | C24—H24A | 0.9600 |
| C10—H10B | 0.9600 | C24—H24B | 0.9600 |
| C10—H10C | 0.9600 | C24—H24C | 0.9600 |
| C7—O1—C1 | 119.0 (2) | O2—C13—H13A | 108.8 |
| N3—O2—C13 | 108.3 (2) | C14—C13—H13A | 108.8 |
| C20—O4—C21 | 122.9 (2) | O2—C13—H13B | 108.8 |
| C7—N1—N2 | 111.3 (2) | C14—C13—H13B | 108.8 |
| C7—N1—C11 | 128.0 (3) | H13A—C13—H13B | 107.7 |
| N2—N1—C11 | 120.7 (3) | C19—C14—C15 | 118.4 (3) |
| C9—N2—N1 | 105.4 (2) | C19—C14—C13 | 123.2 (3) |
| C12—N3—O2 | 110.3 (2) | C15—C14—C13 | 118.4 (3) |
| C2—C1—C6 | 121.1 (3) | C16—C15—C14 | 121.0 (3) |
| C2—C1—O1 | 114.9 (2) | C16—C15—H15 | 119.5 |
| C6—C1—O1 | 123.9 (2) | C14—C15—H15 | 119.5 |
| C1—C2—C3 | 118.8 (3) | C15—C16—C17 | 120.4 (3) |
| C1—C2—H2 | 120.6 | C15—C16—H16 | 119.8 |
| C3—C2—H2 | 120.6 | C17—C16—H16 | 119.8 |
| C4—C3—C2 | 120.8 (3) | C16—C17—C18 | 118.6 (3) |
| C4—C3—H3 | 119.6 | C16—C17—C20 | 122.8 (3) |
| C2—C3—H3 | 119.6 | C18—C17—C20 | 118.6 (3) |
| C3—C4—C5 | 119.7 (3) | C19—C18—C17 | 120.8 (3) |
| C3—C4—H4 | 120.2 | C19—C18—H18 | 119.6 |
| C5—C4—H4 | 120.2 | C17—C18—H18 | 119.6 |
| C4—C5—C6 | 121.0 (3) | C18—C19—C14 | 120.8 (3) |
| C4—C5—H5 | 119.5 | C18—C19—H19 | 119.6 |
| C6—C5—H5 | 119.5 | C14—C19—H19 | 119.6 |
| C1—C6—C5 | 118.5 (3) | O3—C20—O4 | 124.4 (3) |
| C1—C6—H6 | 120.7 | O3—C20—C17 | 123.4 (3) |
| C5—C6—H6 | 120.7 | O4—C20—C17 | 112.1 (3) |
| N1—C7—O1 | 121.8 (2) | O4—C21—C24 | 108.7 (2) |
| N1—C7—C8 | 108.6 (3) | O4—C21—C23 | 102.6 (2) |
| O1—C7—C8 | 129.4 (3) | C24—C21—C23 | 111.6 (3) |
| C7—C8—C9 | 103.6 (3) | O4—C21—C22 | 111.5 (2) |
| C7—C8—C12 | 125.5 (3) | C24—C21—C22 | 112.2 (3) |
| C9—C8—C12 | 130.9 (2) | C23—C21—C22 | 109.9 (3) |
| N2—C9—C8 | 111.1 (2) | C21—C22—H22A | 109.5 |
| N2—C9—C10 | 120.4 (3) | C21—C22—H22B | 109.5 |
| C8—C9—C10 | 128.5 (3) | H22A—C22—H22B | 109.5 |
| C9—C10—H10A | 109.5 | C21—C22—H22C | 109.5 |
| C9—C10—H10B | 109.5 | H22A—C22—H22C | 109.5 |
| H10A—C10—H10B | 109.5 | H22B—C22—H22C | 109.5 |
| C9—C10—H10C | 109.5 | C21—C23—H23A | 109.5 |
| H10A—C10—H10C | 109.5 | C21—C23—H23B | 109.5 |
| H10B—C10—H10C | 109.5 | H23A—C23—H23B | 109.5 |
| N1—C11—H11A | 109.5 | C21—C23—H23C | 109.5 |
| N1—C11—H11B | 109.5 | H23A—C23—H23C | 109.5 |
| H11A—C11—H11B | 109.5 | H23B—C23—H23C | 109.5 |
| N1—C11—H11C | 109.5 | C21—C24—H24A | 109.5 |
| H11A—C11—H11C | 109.5 | C21—C24—H24B | 109.5 |
| H11B—C11—H11C | 109.5 | H24A—C24—H24B | 109.5 |
| N3—C12—C8 | 121.5 (3) | C21—C24—H24C | 109.5 |
| N3—C12—H12 | 119.3 | H24A—C24—H24C | 109.5 |
| C8—C12—H12 | 119.3 | H24B—C24—H24C | 109.5 |
| O2—C13—C14 | 114.0 (2) | ||
| C7—N1—N2—C9 | −0.4 (3) | C7—C8—C9—C10 | −176.7 (3) |
| C11—N1—N2—C9 | 177.3 (3) | C12—C8—C9—C10 | 1.2 (5) |
| C13—O2—N3—C12 | −172.9 (2) | O2—N3—C12—C8 | −178.9 (2) |
| C7—O1—C1—C2 | −171.4 (2) | C7—C8—C12—N3 | −160.1 (3) |
| C7—O1—C1—C6 | 10.0 (4) | C9—C8—C12—N3 | 22.4 (4) |
| C6—C1—C2—C3 | −0.9 (4) | N3—O2—C13—C14 | −73.9 (3) |
| O1—C1—C2—C3 | −179.5 (3) | O2—C13—C14—C19 | −3.9 (4) |
| C1—C2—C3—C4 | 0.2 (5) | O2—C13—C14—C15 | 176.7 (3) |
| C2—C3—C4—C5 | 0.4 (5) | C19—C14—C15—C16 | 0.7 (5) |
| C3—C4—C5—C6 | −0.3 (5) | C13—C14—C15—C16 | −179.9 (3) |
| C2—C1—C6—C5 | 0.9 (4) | C14—C15—C16—C17 | −1.3 (5) |
| O1—C1—C6—C5 | 179.5 (2) | C15—C16—C17—C18 | 0.8 (4) |
| C4—C5—C6—C1 | −0.3 (4) | C15—C16—C17—C20 | 179.0 (3) |
| N2—N1—C7—O1 | −173.2 (2) | C16—C17—C18—C19 | 0.3 (4) |
| C11—N1—C7—O1 | 9.3 (4) | C20—C17—C18—C19 | −178.0 (3) |
| N2—N1—C7—C8 | 1.2 (3) | C17—C18—C19—C14 | −0.8 (4) |
| C11—N1—C7—C8 | −176.3 (3) | C15—C14—C19—C18 | 0.4 (4) |
| C1—O1—C7—N1 | −93.0 (3) | C13—C14—C19—C18 | −179.1 (3) |
| C1—O1—C7—C8 | 93.9 (3) | C21—O4—C20—O3 | 2.1 (5) |
| N1—C7—C8—C9 | −1.4 (3) | C21—O4—C20—C17 | −175.1 (2) |
| O1—C7—C8—C9 | 172.5 (3) | C16—C17—C20—O3 | 177.0 (3) |
| N1—C7—C8—C12 | −179.4 (2) | C18—C17—C20—O3 | −4.8 (4) |
| O1—C7—C8—C12 | −5.6 (4) | C16—C17—C20—O4 | −5.7 (4) |
| N1—N2—C9—C8 | −0.5 (3) | C18—C17—C20—O4 | 172.4 (2) |
| N1—N2—C9—C10 | 177.6 (2) | C20—O4—C21—C24 | 65.5 (4) |
| C7—C8—C9—N2 | 1.2 (3) | C20—O4—C21—C23 | −176.2 (3) |
| C12—C8—C9—N2 | 179.0 (3) | C20—O4—C21—C22 | −58.7 (4) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2396).
References
- Bruker (1999). SMART (Version 5.618), SAINT (Version 6.45), SADABS and SHELXTL (Version 6.1). Bruker AXS Inc., Madison, Wisconsin, USA.
- Lewis, R. J., Camilleri, P., Kirby, A. J., Marby, C. A., Slawin, A. A. & Williams, D. J. (1991). J. Chem. Soc. Perkin Trans. 2, pp. 1625–1631.
- Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
- Zou, X.-M., Lin, D., Pei, J., Wang, C.-Q. & Yang, H.-Z. (2006). Acta Cryst. E62, o2471–o2472.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680705427X/sj2396sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S160053680705427X/sj2396Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report