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In the title compounds, C18H20N2O2, (I), and C14H11N3O4·0.5H2O, (II), respectively, the oxime groups have an E configuration. In (I), the mol­ecules exist as polymers bound by intermolecular C—H...O and O—H...N hydrogen bonds around inversion centres. In (II), intermolecular OW—H...N, OW—H...O and O—H...OW interactions stabilize the molecular packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104017366/ga1061sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104017366/ga1061Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104017366/ga1061IIsup3.hkl
Contains datablock II

CCDC references: 251340; 251341

Comment top

The oxime group (CN—OH) possesses stronger hydrogen-bonding capabilities than alcohols, phenols and carboxylic acids (Marsman et al., 1999). Intermolecular hydrogen bonding has received considerable attention among the range of directional non-covalent intermolecular interactions, which combine moderate strength and directionality, in designing compounds to form supramolecular structures (Karle et al., 1996). The crystal structure determination of the title compounds, N1-(4-tert-butylphenyl)-N2-hydroxy-α-oxo-α-phenylacetamidine, (I), and N1-(4-nitrophenyl)-N2-hydroxy-α-oxo-α-phenylacetamidine hemihydrate, (IIA) and (IIB) (two independent molecules), were carried out to determine the strength of the hydrogen-bonding capabilities of the oxime group, to establish the molecular arrangements, and also to compare the geometry of the oxime moiety with those found in the related compounds 2-[benzoyl(hydroxyimino)methylamino]benzoic acid, (III) (Soylu Taş Batı et al., 2004), and N1-(2,6-dimethylphenyl)-N2-hydroxy-α-oxo-α-phenylacetamidine, (IV) (Soylu Taş Saraco~glu et al., 2004). \sch

Compound (I) crystallizes in the triclinic space group P1 (Fig. 1), whereas compound (II) crystallizes in the monoclinic space group P21/n, with two independent molecules in the asymmetric unit (Fig. 3). Both compounds consist of two phenyl rings linked through an oxime moiety. The interplanar angles between the oxime moiety and the benzene rings are listed in Table 3.

While rings B (C3—C8) and C (C9—C14) are nearly perpendicular to each other in these and the above-mentioned related compounds, those in (IIA) and (IIB) are much more coplanar than those in (I). The oxime moiety in (I) and (IIA) and (IIB) has an E conformation, with appropriate C2—C1N1—O1 torsion angles. There are no significant differences in the C1N1 bond distances or in the C2—C1N1 bond angles (Table 3). The bond lengths and angles of the oxime moiety in (I) are in close accord with the reported values for (III).

Analysis of the crystal packing of (I) and (II) shows significant differences. The molecules of (I) are linked by a nearly linear O—H···N hydrogen bond and a rather weak C—H···O hydrogen bond (Table 1). Atom O1 of the oxime group behaves as a donor, resulting in the formation of O1—H1O···N1 hydrogen bonds which link two molecules related by an inversion centre, an R22(6)-type dimeric arrangement; the intermolecular C10—H10···O2(x − 1, y, z) hydrogen bond is type C11(7) (Bernstein et al., 1995). This interaction links the dimers along the a axis and, as a consequence of this hydrogen bond, the molecules form interesting polymers approximately along the a axis in the crystal, as illustrated in Fig. 2.

In compound (II), the water O atom, O1W, is involved in four hydrogen bonds, two as a donor and two as an acceptor (Table 2 and Fig. 4). There are close contacts between the water and hydroxy groups (H1A—H1W and H1B—H2W). This may relate to the observed disorder of the water H atoms. The crystal packing is therefore stabilized by intermolecular hydrogen bonds, which form a polymeric arrangement parallel to the a axis. While compound (I) forms a polymeric arrangement of symmetry-related molecules, compound (II) arranges polymeric chains of molecules with solvate water molecules, suggesting the hydrogen-bonding interactions in (II) are stronger than in (I). Weak dipole-dipole and van der Waals interactions are also present in both compounds.

Experimental top

Compound (I) was prepared as follows. To a solution of 4-tert-butylanilinin (0.15 mol, 2.24 g) in ethanol (10 ml) was added dropwise a solution of ω-chloroisonitrosoacetophenone (2.75 g, 0.015 mol) in ethanol (20 ml). NaHCO3 (1.10 g) was added to the solution. The precipated product was filtered off and the resulting solution was allowed to stand for 1 h at room temperature for crystallization to occur. Compound (II) was prepared from a mixture of w-chloroisonitrosoacetophenone (2.75 g, 0.015 mol) and NaHCO3 (1.10 g, 0.015 mol) in p-nitroanilyn (0.015 mol, 1.38 g) dissolved in ethanol (10 ml). The precipitate was stirred for 4 h and dissolved in water (10 ml). The crystallized product was filtered off, washed with ethanol and dried.

Refinement top

In compound (I), C-bound H atoms were positioned geometrically and refined as a riding model, with C—H distances in the range 0.93–0.96 Å and with Uiso(H) = 1.2Ueq or 1.5Ueq of the parent atom. The remaining H atoms were located by difference Fourier methods and refined with isotropic displacement parameters. In the final stages of refinement for compound (II), the H atoms on O1A, O1B and the phenyl groups were placed in calculated positions and refined using a riding model, with X—H distances of 0.82 and 0.93 Å, respectively, and with Uiso(H) = 1.2Ueq of the parent atom. The water H atoms were disordered and restraints (O—H = 0.82 Å and H—H = 1.30 Å) were applied to them. They were located by difference Fourier methods and refined with isotropic displacement parameters.

Computing details top

For both compounds, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A view of the hydrogen-bonding interactions in (I). For the sake of clarity, all H atoms, except for H8 and H1O, have been omitted. [Symmetry codes: (i) 2 − x, −y, 1 − z; (ii) x − 1, y, z.]
[Figure 3] Fig. 3. A view of the two independent molecules of (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 4] Fig. 4. A view of the hydrogen-bonding interactions in (II). For the sake of clarity, H atoms bonded to C atoms have been omitted. [Symmetry codes: (i) x − 1/2, 1/2 − y, 1/2 + z; (ii) 1/2 − x, y − 1/2, 1/2 − z; (iii) 2 − x, 1 − y, 1 − z; (iv) x, y, z; (v) x − 1, y, z)].
(I) N1-(4-tert-Butylphenyl)-N2-hydroxy-α-oxo-α-phenylacetamidine top
Crystal data top
C18H20N2O2Z = 2
Mr = 296.36F(000) = 316
Triclinic, P1Dx = 1.236 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.4331 (10) ÅCell parameters from 4848 reflections
b = 10.7150 (15) Åθ = 2.0–26.8°
c = 12.299 (2) ŵ = 0.08 mm1
α = 75.054 (12)°T = 293 K
β = 82.120 (12)°Rod, yellow
γ = 77.258 (11)°0.42 × 0.19 × 0.05 mm
V = 796.0 (2) Å3
Data collection top
Stoe IPDS 2
diffractometer
1403 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.093
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
Detector resolution: 6.67 pixels mm-1h = 77
ϕ scansk = 1212
10299 measured reflectionsl = 1414
2808 independent 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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0381P)2]
where P = (Fo2 + 2Fc2)/3
2808 reflections(Δ/σ)max < 0.001
207 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C18H20N2O2γ = 77.258 (11)°
Mr = 296.36V = 796.0 (2) Å3
Triclinic, P1Z = 2
a = 6.4331 (10) ÅMo Kα radiation
b = 10.7150 (15) ŵ = 0.08 mm1
c = 12.299 (2) ÅT = 293 K
α = 75.054 (12)°0.42 × 0.19 × 0.05 mm
β = 82.120 (12)°
Data collection top
Stoe IPDS 2
diffractometer
1403 reflections with I > 2σ(I)
10299 measured reflectionsRint = 0.093
2808 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.13 e Å3
2808 reflectionsΔρmin = 0.21 e Å3
207 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
N11.0008 (4)0.1449 (2)0.4568 (2)0.0436 (7)
N20.8023 (5)0.3598 (2)0.4180 (3)0.0495 (8)
O10.8108 (4)0.1207 (2)0.5250 (2)0.0557 (7)
O21.3367 (4)0.3021 (2)0.3709 (2)0.0561 (7)
C10.9814 (5)0.2679 (3)0.4085 (3)0.0375 (8)
C21.1764 (5)0.3008 (3)0.3307 (3)0.0390 (8)
C31.1644 (5)0.3210 (3)0.2085 (3)0.0402 (8)
C40.9908 (6)0.2968 (3)0.1664 (3)0.0518 (9)
H40.87560.27210.21550.062*
C50.9896 (7)0.3093 (4)0.0524 (3)0.0659 (11)
H50.87430.29210.02460.079*
C61.1580 (8)0.3472 (4)0.0204 (4)0.0726 (12)
H61.15600.35690.09760.087*
C71.3293 (7)0.3706 (4)0.0211 (4)0.0732 (12)
H71.44390.39530.02850.088*
C81.3342 (6)0.3581 (3)0.1344 (3)0.0564 (10)
H81.45120.37450.16150.068*
C90.7698 (5)0.4966 (3)0.3703 (3)0.0366 (8)
C100.5712 (5)0.5613 (3)0.3357 (3)0.0492 (9)
H100.46330.51410.34190.059*
C110.5313 (5)0.6955 (3)0.2921 (3)0.0474 (9)
H110.39500.73680.27080.057*
C120.6850 (5)0.7710 (3)0.2787 (2)0.0349 (7)
C130.8820 (5)0.7039 (3)0.3160 (3)0.0416 (8)
H130.99000.75110.31000.050*
C140.9247 (5)0.5697 (3)0.3617 (3)0.0435 (8)
H141.05860.52880.38670.052*
C150.6424 (5)0.9203 (3)0.2287 (3)0.0405 (8)
C160.4223 (6)0.9697 (3)0.1826 (3)0.0654 (11)
H16A0.40161.06310.15190.098*
H16B0.31340.95040.24260.098*
H16C0.41380.92660.12440.098*
C170.8119 (6)0.9551 (3)0.1315 (3)0.0686 (11)
H17A0.78451.04850.10050.103*
H17B0.80630.91060.07380.103*
H17C0.95110.92810.15940.103*
C180.6534 (6)0.9902 (3)0.3209 (3)0.0630 (11)
H18A0.62721.08370.29020.095*
H18B0.79270.96230.34860.095*
H18C0.54710.96860.38180.095*
H1N0.693 (5)0.330 (3)0.445 (3)0.049 (11)*
H1O0.836 (6)0.031 (4)0.545 (3)0.098 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0473 (17)0.0299 (15)0.0480 (17)0.0090 (13)0.0058 (15)0.0029 (13)
N20.0443 (18)0.0255 (14)0.067 (2)0.0055 (15)0.0125 (17)0.0008 (14)
O10.0621 (16)0.0313 (13)0.0611 (16)0.0094 (12)0.0176 (13)0.0003 (12)
O20.0463 (14)0.0514 (14)0.0713 (17)0.0130 (12)0.0104 (13)0.0100 (12)
C10.046 (2)0.0261 (16)0.039 (2)0.0059 (15)0.0039 (16)0.0070 (14)
C20.0361 (19)0.0209 (15)0.057 (2)0.0030 (14)0.0018 (17)0.0064 (15)
C30.0453 (19)0.0259 (15)0.048 (2)0.0059 (14)0.0010 (17)0.0089 (15)
C40.058 (2)0.0438 (19)0.054 (2)0.0108 (17)0.0034 (19)0.0153 (18)
C50.088 (3)0.056 (2)0.060 (3)0.018 (2)0.006 (2)0.021 (2)
C60.114 (4)0.051 (2)0.048 (3)0.014 (2)0.008 (3)0.013 (2)
C70.087 (3)0.061 (2)0.065 (3)0.021 (2)0.027 (2)0.016 (2)
C80.061 (2)0.047 (2)0.061 (3)0.0194 (19)0.015 (2)0.0130 (19)
C90.0418 (19)0.0237 (15)0.042 (2)0.0041 (14)0.0055 (16)0.0096 (14)
C100.038 (2)0.0328 (18)0.074 (3)0.0116 (16)0.0013 (19)0.0084 (17)
C110.0358 (19)0.0345 (18)0.067 (2)0.0025 (15)0.0071 (18)0.0045 (17)
C120.0391 (18)0.0283 (15)0.0358 (19)0.0042 (15)0.0013 (15)0.0078 (14)
C130.0398 (19)0.0335 (17)0.053 (2)0.0082 (15)0.0074 (17)0.0096 (16)
C140.0389 (19)0.0302 (17)0.060 (2)0.0025 (15)0.0097 (17)0.0089 (16)
C150.049 (2)0.0263 (15)0.043 (2)0.0049 (14)0.0044 (16)0.0044 (14)
C160.067 (3)0.0386 (19)0.082 (3)0.0006 (18)0.026 (2)0.0010 (19)
C170.081 (3)0.044 (2)0.070 (3)0.014 (2)0.011 (2)0.0002 (19)
C180.083 (3)0.0366 (18)0.072 (3)0.0099 (18)0.008 (2)0.0178 (19)
Geometric parameters (Å, º) top
N1—C11.283 (3)C10—C111.378 (4)
N1—O11.418 (3)C10—H100.9300
N2—C11.354 (4)C11—C121.378 (4)
N2—C91.411 (4)C11—H110.9300
N2—H1N0.83 (3)C12—C131.386 (4)
O1—H1O0.91 (4)C12—C151.535 (4)
O2—C21.208 (3)C13—C141.382 (4)
C1—C21.518 (4)C13—H130.9300
C2—C31.473 (4)C14—H140.9300
C3—C81.383 (4)C15—C181.529 (4)
C3—C41.392 (4)C15—C161.530 (4)
C4—C51.375 (5)C15—C171.532 (5)
C4—H40.9300C16—H16A0.9600
C5—C61.371 (5)C16—H16B0.9600
C5—H50.9300C16—H16C0.9600
C6—C71.371 (6)C17—H17A0.9600
C6—H60.9300C17—H17B0.9600
C7—C81.370 (5)C17—H17C0.9600
C7—H70.9300C18—H18A0.9600
C8—H80.9300C18—H18B0.9600
C9—C141.376 (4)C18—H18C0.9600
C9—C101.378 (4)
C1—N1—O1110.1 (3)C10—C11—H11118.7
C1—N2—C9128.3 (3)C12—C11—H11118.7
C1—N2—H1N115 (2)C11—C12—C13115.6 (3)
C9—N2—H1N116 (2)C11—C12—C15122.9 (3)
N1—O1—H1O101 (3)C13—C12—C15121.5 (3)
N1—C1—N2124.8 (3)C14—C13—C12122.7 (3)
N1—C1—C2113.2 (3)C14—C13—H13118.6
N2—C1—C2121.9 (3)C12—C13—H13118.6
O2—C2—C3122.9 (3)C9—C14—C13120.2 (3)
O2—C2—C1119.4 (3)C9—C14—H14119.9
C3—C2—C1117.6 (3)C13—C14—H14119.9
C8—C3—C4119.3 (3)C18—C15—C16108.8 (3)
C8—C3—C2119.3 (3)C18—C15—C17109.3 (3)
C4—C3—C2121.3 (3)C16—C15—C17108.1 (3)
C5—C4—C3120.0 (4)C18—C15—C12108.9 (3)
C5—C4—H4120.0C16—C15—C12111.9 (3)
C3—C4—H4120.0C17—C15—C12109.8 (3)
C6—C5—C4120.2 (4)C15—C16—H16A109.5
C6—C5—H5119.9C15—C16—H16B109.5
C4—C5—H5119.9H16A—C16—H16B109.5
C5—C6—C7119.8 (4)C15—C16—H16C109.5
C5—C6—H6120.1H16A—C16—H16C109.5
C7—C6—H6120.1H16B—C16—H16C109.5
C8—C7—C6121.0 (4)C15—C17—H17A109.5
C8—C7—H7119.5C15—C17—H17B109.5
C6—C7—H7119.5H17A—C17—H17B109.5
C7—C8—C3119.7 (4)C15—C17—H17C109.5
C7—C8—H8120.2H17A—C17—H17C109.5
C3—C8—H8120.2H17B—C17—H17C109.5
C14—C9—C10118.3 (3)C15—C18—H18A109.5
C14—C9—N2122.8 (3)C15—C18—H18B109.5
C10—C9—N2118.8 (3)H18A—C18—H18B109.5
C11—C10—C9120.5 (3)C15—C18—H18C109.5
C11—C10—H10119.7H18A—C18—H18C109.5
C9—C10—H10119.7H18B—C18—H18C109.5
C10—C11—C12122.7 (3)
O1—N1—C1—N22.4 (4)C2—C3—C8—C7176.6 (3)
O1—N1—C1—C2178.0 (3)C1—N2—C9—C1438.1 (5)
C9—N2—C1—N1178.3 (3)C1—N2—C9—C10145.2 (3)
C9—N2—C1—C26.5 (5)C14—C9—C10—C111.0 (5)
N1—C1—C2—O274.6 (4)N2—C9—C10—C11177.9 (3)
N2—C1—C2—O2109.7 (3)C9—C10—C11—C121.2 (5)
N1—C1—C2—C3101.4 (3)C10—C11—C12—C132.3 (5)
N2—C1—C2—C374.4 (4)C10—C11—C12—C15179.1 (3)
O2—C2—C3—C87.7 (4)C11—C12—C13—C141.2 (5)
C1—C2—C3—C8176.5 (3)C15—C12—C13—C14179.8 (3)
O2—C2—C3—C4168.8 (3)C10—C9—C14—C132.0 (5)
C1—C2—C3—C47.0 (4)N2—C9—C14—C13178.8 (3)
C8—C3—C4—C50.2 (5)C12—C13—C14—C90.9 (5)
C2—C3—C4—C5176.3 (3)C11—C12—C15—C18112.9 (3)
C3—C4—C5—C60.7 (5)C13—C12—C15—C1865.6 (4)
C4—C5—C6—C71.0 (6)C11—C12—C15—C167.3 (4)
C5—C6—C7—C80.7 (6)C13—C12—C15—C16174.2 (3)
C6—C7—C8—C30.2 (6)C11—C12—C15—C17127.4 (3)
C4—C3—C8—C70.1 (5)C13—C12—C15—C1754.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N1i0.91 (4)1.95 (4)2.801 (3)155 (4)
C10—H10···O2ii0.932.503.351 (4)152
Symmetry codes: (i) x+2, y, z+1; (ii) x1, y, z.
(II) N1-(4-nitrophenyl)-N2-hydroxy-α-oxo-α-phenylacetamidine hemihydrate top
Crystal data top
C14H11N3O4·0.5H2OF(000) = 1224
Mr = 294.27Dx = 1.412 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5334 reflections
a = 6.8298 (5) Åθ = 1.5–24.0°
b = 15.5454 (15) ŵ = 0.11 mm1
c = 26.097 (2) ÅT = 293 K
β = 92.080 (7)°Rod, yellow
V = 2769.0 (4) Å30.40 × 0.22 × 0.12 mm
Z = 8
Data collection top
Stoe IPDS 2
diffractometer
1986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.067
Graphite monochromatorθmax = 25.0°, θmin = 1.5°
Detector resolution: 6.67 pixels mm-1h = 87
ϕ scansk = 1818
17727 measured reflectionsl = 3030
4876 independent 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047H atoms treated by a mixture of independent and constrained refinement
S = 0.81 w = 1/[σ2(Fo2) + (0.005P)2]
where P = (Fo2 + 2Fc2)/3
4876 reflections(Δ/σ)max < 0.001
402 parametersΔρmax = 0.17 e Å3
3 restraintsΔρmin = 0.13 e Å3
Crystal data top
C14H11N3O4·0.5H2OV = 2769.0 (4) Å3
Mr = 294.27Z = 8
Monoclinic, P21/nMo Kα radiation
a = 6.8298 (5) ŵ = 0.11 mm1
b = 15.5454 (15) ÅT = 293 K
c = 26.097 (2) Å0.40 × 0.22 × 0.12 mm
β = 92.080 (7)°
Data collection top
Stoe IPDS 2
diffractometer
1986 reflections with I > 2σ(I)
17727 measured reflectionsRint = 0.067
4876 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0363 restraints
wR(F2) = 0.047H atoms treated by a mixture of independent and constrained refinement
S = 0.81Δρmax = 0.17 e Å3
4876 reflectionsΔρmin = 0.13 e Å3
402 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
N1A0.6637 (3)0.21335 (12)0.06230 (7)0.0468 (5)
N1B1.1720 (3)0.48109 (12)0.44398 (7)0.0450 (5)
N2A0.3680 (3)0.28571 (15)0.04058 (9)0.0548 (6)
N2B0.8674 (3)0.52025 (14)0.40480 (8)0.0506 (6)
N3A0.2515 (4)0.51018 (16)0.07792 (11)0.0755 (8)
N3B0.3301 (4)0.49047 (17)0.23707 (10)0.0755 (8)
O1A0.6753 (2)0.21744 (9)0.00884 (6)0.0559 (5)
H1A0.77580.19350.00010.067*
O1B1.1814 (2)0.57043 (9)0.45172 (6)0.0578 (5)
H1B1.28360.58260.46750.069*
O2A0.2934 (3)0.21893 (11)0.14050 (6)0.0643 (5)
O2B0.8037 (2)0.34278 (10)0.42569 (6)0.0569 (5)
O3A0.2412 (3)0.55168 (15)0.11732 (10)0.1268 (10)
O3B0.3724 (4)0.44530 (17)0.20195 (8)0.1377 (11)
O4A0.3882 (3)0.51435 (16)0.04786 (9)0.1254 (9)
O4B0.1757 (3)0.52825 (14)0.23839 (8)0.1041 (8)
C1A0.5052 (4)0.25141 (14)0.07535 (9)0.0448 (7)
C1B1.0103 (4)0.46190 (14)0.41877 (8)0.0405 (6)
C2A0.4609 (4)0.23725 (15)0.13059 (10)0.0482 (7)
C2B0.9639 (4)0.36698 (15)0.41305 (9)0.0421 (6)
C3A0.6226 (4)0.24078 (15)0.17016 (9)0.0462 (7)
C3B1.1074 (4)0.30725 (14)0.39264 (8)0.0385 (6)
C4A0.7902 (4)0.28831 (15)0.16430 (9)0.0559 (7)
H4A0.80600.31880.13400.067*
C4B1.2769 (4)0.33354 (15)0.37044 (8)0.0497 (7)
H4B1.30650.39180.36860.060*
C5A0.9361 (4)0.29172 (17)0.20264 (11)0.0646 (8)
H5A1.04690.32530.19820.078*
C5B1.4026 (4)0.27384 (17)0.35089 (10)0.0629 (8)
H5B1.51690.29180.33580.075*
C6A0.9175 (5)0.24537 (18)0.24738 (11)0.0697 (9)
H6A1.01580.24680.27300.084*
C6B1.3594 (4)0.18755 (17)0.35361 (10)0.0672 (8)
H6B1.44600.14730.34100.081*
C7A0.7514 (5)0.19724 (18)0.25344 (10)0.0697 (9)
H7A0.73830.16510.28320.084*
C7B1.1899 (4)0.16057 (16)0.37478 (10)0.0645 (8)
H7B1.15990.10230.37590.077*
C8A0.6031 (4)0.19601 (16)0.21579 (10)0.0607 (8)
H8A0.48930.16490.22110.073*
C8B1.0649 (4)0.21966 (15)0.39429 (9)0.0508 (7)
H8B0.94990.20120.40890.061*
C9A0.2154 (4)0.34336 (15)0.04977 (9)0.0458 (7)
C9B0.7353 (4)0.51216 (14)0.36248 (9)0.0413 (6)
C10A0.0580 (4)0.34881 (16)0.01453 (9)0.0556 (7)
H10A0.05650.31510.01490.067*
C10B0.7754 (4)0.45955 (15)0.32140 (9)0.0500 (7)
H10B0.89240.42890.32120.060*
C11A0.0958 (4)0.40396 (16)0.02309 (10)0.0569 (8)
H11A0.20160.40830.00020.068*
C11B0.6416 (4)0.45255 (15)0.28064 (9)0.0546 (7)
H11B0.66710.41640.25330.066*
C12A0.0872 (4)0.45233 (16)0.06732 (11)0.0505 (7)
C12B0.4720 (4)0.49889 (16)0.28059 (9)0.0493 (7)
C13A0.0691 (4)0.44942 (15)0.10171 (9)0.0540 (7)
H13A0.07080.48390.13090.065*
C13B0.4321 (3)0.55364 (15)0.31996 (9)0.0494 (7)
H13B0.31720.58580.31920.059*
C14A0.2233 (4)0.39539 (14)0.09293 (9)0.0504 (7)
H14A0.33150.39370.11560.061*
C14B0.5656 (3)0.56039 (14)0.36105 (8)0.0460 (7)
H14B0.54060.59770.38790.055*
H2A0.374 (4)0.2753 (15)0.0101 (8)0.059 (9)*
H2B0.878 (3)0.5682 (12)0.4206 (7)0.036 (7)*
O1W0.0046 (3)0.88833 (12)0.01269 (6)0.0569 (5)
H1W0.095 (2)0.9175 (13)0.0253 (8)0.068*
H2W0.072 (3)0.8771 (16)0.0346 (7)0.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0548 (16)0.0497 (13)0.0363 (13)0.0060 (12)0.0070 (11)0.0029 (11)
N1B0.0436 (14)0.0381 (12)0.0533 (13)0.0019 (11)0.0006 (11)0.0076 (10)
N2A0.0617 (17)0.0602 (16)0.0425 (15)0.0136 (13)0.0020 (14)0.0037 (14)
N2B0.0500 (15)0.0401 (14)0.0606 (15)0.0103 (12)0.0128 (12)0.0183 (12)
N3A0.0561 (19)0.0680 (19)0.102 (2)0.0049 (16)0.0020 (18)0.0047 (17)
N3B0.078 (2)0.079 (2)0.0682 (19)0.0118 (16)0.0214 (18)0.0129 (15)
O1A0.0572 (12)0.0622 (11)0.0492 (11)0.0039 (9)0.0144 (9)0.0071 (9)
O1B0.0509 (12)0.0423 (11)0.0790 (12)0.0025 (9)0.0155 (10)0.0153 (9)
O2A0.0517 (13)0.0718 (13)0.0705 (13)0.0008 (11)0.0164 (11)0.0127 (10)
O2B0.0413 (12)0.0539 (11)0.0763 (13)0.0029 (10)0.0126 (10)0.0085 (9)
O3A0.0913 (19)0.129 (2)0.159 (2)0.0518 (16)0.0166 (18)0.0615 (19)
O3B0.141 (2)0.183 (3)0.0850 (17)0.0624 (19)0.0523 (16)0.0738 (18)
O4A0.0701 (16)0.162 (2)0.143 (2)0.0417 (16)0.0228 (16)0.0105 (18)
O4B0.0893 (18)0.1190 (19)0.1005 (17)0.0293 (15)0.0454 (16)0.0298 (14)
C1A0.0443 (18)0.0406 (16)0.0500 (17)0.0039 (13)0.0065 (15)0.0025 (13)
C1B0.0427 (16)0.0369 (16)0.0422 (15)0.0026 (14)0.0060 (13)0.0059 (12)
C2A0.059 (2)0.0375 (15)0.0490 (18)0.0032 (15)0.0125 (16)0.0020 (13)
C2B0.0395 (17)0.0442 (16)0.0424 (16)0.0002 (14)0.0029 (13)0.0043 (12)
C3A0.0522 (18)0.0439 (16)0.0433 (16)0.0035 (14)0.0130 (14)0.0004 (13)
C3B0.0403 (16)0.0383 (16)0.0369 (15)0.0008 (13)0.0003 (13)0.0040 (12)
C4A0.061 (2)0.0551 (18)0.0520 (17)0.0036 (16)0.0052 (17)0.0031 (15)
C4B0.056 (2)0.0398 (15)0.0535 (17)0.0063 (15)0.0072 (15)0.0035 (14)
C5A0.058 (2)0.072 (2)0.0642 (19)0.0099 (17)0.0112 (18)0.0082 (17)
C5B0.0533 (19)0.0573 (19)0.080 (2)0.0034 (16)0.0320 (15)0.0117 (16)
C6A0.067 (2)0.087 (2)0.055 (2)0.0163 (19)0.0027 (17)0.0100 (18)
C6B0.063 (2)0.051 (2)0.088 (2)0.0092 (16)0.0153 (18)0.0098 (16)
C7A0.077 (2)0.082 (2)0.0511 (18)0.0087 (19)0.0102 (19)0.0096 (16)
C7B0.071 (2)0.0372 (17)0.087 (2)0.0005 (16)0.0214 (18)0.0023 (16)
C8A0.059 (2)0.072 (2)0.0513 (17)0.0014 (15)0.0142 (17)0.0052 (16)
C8B0.0514 (19)0.0427 (16)0.0595 (17)0.0031 (14)0.0170 (14)0.0009 (14)
C9A0.0506 (19)0.0400 (16)0.0470 (17)0.0033 (14)0.0036 (15)0.0024 (14)
C9B0.0437 (16)0.0364 (15)0.0436 (16)0.0004 (13)0.0024 (14)0.0025 (13)
C10A0.064 (2)0.0525 (19)0.0500 (17)0.0056 (16)0.0060 (16)0.0013 (14)
C10B0.0486 (18)0.0512 (17)0.0499 (16)0.0118 (14)0.0017 (15)0.0063 (14)
C11A0.0462 (19)0.0561 (18)0.068 (2)0.0066 (15)0.0117 (16)0.0157 (16)
C11B0.067 (2)0.0564 (18)0.0404 (16)0.0092 (16)0.0007 (16)0.0098 (14)
C12A0.0417 (18)0.0383 (16)0.0717 (19)0.0013 (14)0.0032 (16)0.0074 (15)
C12B0.0515 (18)0.0528 (18)0.0426 (16)0.0023 (14)0.0097 (14)0.0021 (14)
C13A0.060 (2)0.0420 (17)0.0601 (17)0.0008 (14)0.0010 (17)0.0032 (14)
C13B0.0397 (17)0.0505 (17)0.0576 (17)0.0070 (13)0.0039 (15)0.0007 (14)
C14A0.0521 (18)0.0442 (16)0.0547 (17)0.0029 (14)0.0030 (15)0.0021 (14)
C14B0.0500 (18)0.0384 (15)0.0495 (16)0.0068 (13)0.0017 (15)0.0078 (12)
O1W0.0444 (13)0.0608 (13)0.0654 (13)0.0065 (10)0.0004 (10)0.0033 (10)
Geometric parameters (Å, º) top
N1A—C1A1.290 (3)C5B—C6B1.376 (3)
N1A—O1A1.402 (2)C5B—H5B0.9300
N1B—C1B1.299 (3)C6A—C7A1.373 (3)
N1B—O1B1.4045 (19)C6A—H6A0.9300
N2A—C1A1.387 (3)C6B—C7B1.366 (3)
N2A—C9A1.402 (3)C6B—H6B0.9300
N2A—H2A0.82 (2)C7A—C8A1.385 (3)
N2B—C1B1.372 (3)C7A—H7A0.9300
N2B—C9B1.406 (3)C7B—C8B1.365 (3)
N2B—H2B0.855 (17)C7B—H7B0.9300
N3A—O4A1.200 (3)C8A—H8A0.9300
N3A—O3A1.214 (3)C8B—H8B0.9300
N3A—C12A1.472 (3)C9A—C14A1.386 (3)
N3B—O3B1.198 (3)C9A—C10A1.392 (3)
N3B—O4B1.209 (3)C9B—C14B1.380 (3)
N3B—C12B1.472 (3)C9B—C10B1.384 (3)
O1A—H1A0.8200C10A—C11A1.380 (3)
O1B—H1B0.8200C10A—H10A0.9300
O2A—C2A1.216 (3)C10B—C11B1.381 (3)
O2B—C2B1.214 (3)C10B—H10B0.9300
C1A—C2A1.500 (3)C11A—C12A1.377 (3)
C1B—C2B1.516 (3)C11A—H11A0.9300
C2A—C3A1.485 (3)C11B—C12B1.364 (3)
C2B—C3B1.464 (3)C11B—H11B0.9300
C3A—C4A1.376 (3)C12A—C13A1.370 (3)
C3A—C8A1.390 (3)C12B—C13B1.369 (3)
C3B—C4B1.375 (3)C13A—C14A1.373 (3)
C3B—C8B1.393 (3)C13A—H13A0.9300
C4A—C5A1.387 (3)C13B—C14B1.386 (3)
C4A—H4A0.9300C13B—H13B0.9300
C4B—C5B1.375 (3)C14A—H14A0.9300
C4B—H4B0.9300C14B—H14B0.9300
C5A—C6A1.382 (3)O1W—H1W0.823 (9)
C5A—H5A0.9300O1W—H2W0.809 (9)
C1A—N1A—O1A108.68 (19)C5B—C6B—H6B119.8
C1B—N1B—O1B109.47 (18)C6A—C7A—C8A120.8 (3)
C1A—N2A—C9A128.5 (2)C6A—C7A—H7A119.6
C1A—N2A—H2A120.2 (18)C8A—C7A—H7A119.6
C9A—N2A—H2A111.2 (18)C8B—C7B—C6B119.6 (3)
C1B—N2B—C9B125.4 (2)C8B—C7B—H7B120.2
C1B—N2B—H2B113.6 (13)C6B—C7B—H7B120.2
C9B—N2B—H2B120.0 (13)C7A—C8A—C3A120.7 (3)
O4A—N3A—O3A123.0 (3)C7A—C8A—H8A119.6
O4A—N3A—C12A119.4 (3)C3A—C8A—H8A119.6
O3A—N3A—C12A117.6 (3)C7B—C8B—C3B120.8 (2)
O3B—N3B—O4B122.8 (3)C7B—C8B—H8B119.6
O3B—N3B—C12B118.2 (3)C3B—C8B—H8B119.6
O4B—N3B—C12B119.0 (3)C14A—C9A—C10A120.5 (3)
N1A—O1A—H1A109.5C14A—C9A—N2A120.3 (2)
N1B—O1B—H1B109.5C10A—C9A—N2A119.1 (2)
N1A—C1A—N2A123.8 (2)C14B—C9B—C10B119.3 (2)
N1A—C1A—C2A112.7 (2)C14B—C9B—N2B119.1 (2)
N2A—C1A—C2A122.0 (2)C10B—C9B—N2B121.5 (2)
N1B—C1B—N2B124.5 (2)C11A—C10A—C9A120.3 (3)
N1B—C1B—C2B116.4 (2)C11A—C10A—H10A119.8
N2B—C1B—C2B118.2 (2)C9A—C10A—H10A119.8
O2A—C2A—C3A122.8 (2)C11B—C10B—C9B120.0 (2)
O2A—C2A—C1A117.6 (2)C11B—C10B—H10B120.0
C3A—C2A—C1A119.5 (2)C9B—C10B—H10B120.0
O2B—C2B—C3B121.6 (2)C12A—C11A—C10A117.7 (2)
O2B—C2B—C1B117.5 (2)C12A—C11A—H11A121.1
C3B—C2B—C1B120.8 (2)C10A—C11A—H11A121.1
C4A—C3A—C8A118.0 (2)C12B—C11B—C10B119.8 (2)
C4A—C3A—C2A122.9 (2)C12B—C11B—H11B120.1
C8A—C3A—C2A119.0 (3)C10B—C11B—H11B120.1
C4B—C3B—C8B118.9 (2)C13A—C12A—C11A122.7 (3)
C4B—C3B—C2B123.3 (2)C13A—C12A—N3A118.6 (3)
C8B—C3B—C2B117.7 (2)C11A—C12A—N3A118.8 (3)
C3A—C4A—C5A121.3 (2)C11B—C12B—C13B121.3 (2)
C3A—C4A—H4A119.4C11B—C12B—N3B119.3 (2)
C5A—C4A—H4A119.4C13B—C12B—N3B119.4 (2)
C3B—C4B—C5B120.1 (2)C12A—C13A—C14A119.7 (3)
C3B—C4B—H4B119.9C12A—C13A—H13A120.2
C5B—C4B—H4B119.9C14A—C13A—H13A120.2
C6A—C5A—C4A120.2 (3)C12B—C13B—C14B119.0 (2)
C6A—C5A—H5A119.9C12B—C13B—H13B120.5
C4A—C5A—H5A119.9C14B—C13B—H13B120.5
C4B—C5B—C6B120.0 (3)C13A—C14A—C9A119.0 (2)
C4B—C5B—H5B120.0C13A—C14A—H14A120.5
C6B—C5B—H5B120.0C9A—C14A—H14A120.5
C7A—C6A—C5A118.9 (3)C9B—C14B—C13B120.5 (2)
C7A—C6A—H6A120.5C9B—C14B—H14B119.7
C5A—C6A—H6A120.5C13B—C14B—H14B119.7
C7B—C6B—C5B120.5 (3)H1W—O1W—H2W109.3 (19)
C7B—C6B—H6B119.8
O1A—N1A—C1A—N2A3.1 (3)C2A—C3A—C8A—C7A179.5 (2)
O1A—N1A—C1A—C2A169.90 (17)C6B—C7B—C8B—C3B0.3 (4)
C9A—N2A—C1A—N1A165.0 (2)C4B—C3B—C8B—C7B0.7 (4)
C9A—N2A—C1A—C2A29.4 (4)C2B—C3B—C8B—C7B178.4 (2)
O1B—N1B—C1B—N2B3.5 (3)C1A—N2A—C9A—C14A21.8 (4)
O1B—N1B—C1B—C2B172.33 (18)C1A—N2A—C9A—C10A159.4 (2)
C9B—N2B—C1B—N1B153.1 (2)C1B—N2B—C9B—C14B161.0 (2)
C9B—N2B—C1B—C2B38.2 (3)C1B—N2B—C9B—C10B21.6 (4)
N1A—C1A—C2A—O2A134.7 (2)C14A—C9A—C10A—C11A2.4 (4)
N2A—C1A—C2A—O2A32.4 (3)N2A—C9A—C10A—C11A178.9 (2)
N1A—C1A—C2A—C3A41.7 (3)C14B—C9B—C10B—C11B3.1 (4)
N2A—C1A—C2A—C3A151.3 (2)N2B—C9B—C10B—C11B179.4 (2)
N1B—C1B—C2B—O2B127.7 (2)C9A—C10A—C11A—C12A0.2 (4)
N2B—C1B—C2B—O2B41.9 (3)C9B—C10B—C11B—C12B1.3 (4)
N1B—C1B—C2B—C3B52.7 (3)C10A—C11A—C12A—C13A2.0 (4)
N2B—C1B—C2B—C3B137.7 (2)C10A—C11A—C12A—N3A178.6 (2)
O2A—C2A—C3A—C4A156.7 (3)O4A—N3A—C12A—C13A179.0 (3)
C1A—C2A—C3A—C4A27.1 (4)O3A—N3A—C12A—C13A1.1 (4)
O2A—C2A—C3A—C8A21.6 (4)O4A—N3A—C12A—C11A0.4 (4)
C1A—C2A—C3A—C8A154.5 (2)O3A—N3A—C12A—C11A179.5 (3)
O2B—C2B—C3B—C4B169.3 (2)C10B—C11B—C12B—C13B1.0 (4)
C1B—C2B—C3B—C4B10.2 (3)C10B—C11B—C12B—N3B179.6 (2)
O2B—C2B—C3B—C8B8.2 (3)O3B—N3B—C12B—C11B2.8 (4)
C1B—C2B—C3B—C8B172.3 (2)O4B—N3B—C12B—C11B176.3 (3)
C8A—C3A—C4A—C5A0.0 (4)O3B—N3B—C12B—C13B176.5 (3)
C2A—C3A—C4A—C5A178.4 (2)O4B—N3B—C12B—C13B4.3 (4)
C8B—C3B—C4B—C5B0.8 (4)C11A—C12A—C13A—C14A1.2 (4)
C2B—C3B—C4B—C5B178.3 (2)N3A—C12A—C13A—C14A179.4 (2)
C3A—C4A—C5A—C6A1.5 (4)C11B—C12B—C13B—C14B1.3 (4)
C3B—C4B—C5B—C6B0.2 (4)N3B—C12B—C13B—C14B179.3 (2)
C4A—C5A—C6A—C7A1.0 (4)C12A—C13A—C14A—C9A1.4 (4)
C4B—C5B—C6B—C7B1.3 (4)C10A—C9A—C14A—C13A3.1 (4)
C5A—C6A—C7A—C8A1.0 (4)N2A—C9A—C14A—C13A178.1 (2)
C5B—C6B—C7B—C8B1.4 (4)C10B—C9B—C14B—C13B2.8 (4)
C6A—C7A—C8A—C3A2.6 (4)N2B—C9B—C14B—C13B179.7 (2)
C4A—C3A—C8A—C7A2.0 (4)C12B—C13B—C14B—C9B0.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1Wi0.822.002.808 (3)167
O1B—H1B···O1Wii0.821.932.750 (2)173
O1W—H1W···N1Biii0.82 (2)2.02 (2)2.838 (2)176 (2)
O1W—H2W···O2Biv0.81 (2)2.00 (2)2.787 (2)166 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x+3/2, y+3/2, z+1/2; (iii) x+3/2, y+1/2, z+1/2; (iv) x+1/2, y+1/2, z+1/2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC18H20N2O2C14H11N3O4·0.5H2O
Mr296.36294.27
Crystal system, space groupTriclinic, P1Monoclinic, P21/n
Temperature (K)293293
a, b, c (Å)6.4331 (10), 10.7150 (15), 12.299 (2)6.8298 (5), 15.5454 (15), 26.097 (2)
α, β, γ (°)75.054 (12), 82.120 (12), 77.258 (11)90, 92.080 (7), 90
V3)796.0 (2)2769.0 (4)
Z28
Radiation typeMo KαMo Kα
µ (mm1)0.080.11
Crystal size (mm)0.42 × 0.19 × 0.050.40 × 0.22 × 0.12
Data collection
DiffractometerStoe IPDS 2
diffractometer
Stoe IPDS 2
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10299, 2808, 1403 17727, 4876, 1986
Rint0.0930.067
(sin θ/λ)max1)0.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.114, 0.95 0.036, 0.047, 0.81
No. of reflections28084876
No. of parameters207402
No. of restraints03
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.13, 0.210.17, 0.13

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N1i0.91 (4)1.95 (4)2.801 (3)155 (4)
C10—H10···O2ii0.932.503.351 (4)152
Symmetry codes: (i) x+2, y, z+1; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1Wi0.822.002.808 (3)167
O1B—H1B···O1Wii0.821.932.750 (2)173
O1W—H1W···N1Biii0.82 (2)2.02 (2)2.838 (2)176 (2)
O1W—H2W···O2Biv0.81 (2)2.00 (2)2.787 (2)166 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x+3/2, y+3/2, z+1/2; (iii) x+3/2, y+1/2, z+1/2; (iv) x+1/2, y+1/2, z+1/2.
Comparison of geometric parameters (Å, °) for (I) and (II) with those in the related compounds (III) and (VI) top
Bond(I)(IIA)(IIB)(III)(IV)
C1—N11.283 (3)1.290 (3)1.299 (3)1.288 (2)1.295 (3)
N1—O11.418 (3)1.402 (2)1.404 (2)1.4093 (18)1.413 (3)
C2—C11.518 (4)1.500 (3)1.516 (3)1.501 (2)1.494 (4)
C1—N1—O1110.1 (3)108.68 (19)109.47 (18)111.51 (13)109.97 (19)
C2—C1—N1113.2 (3)112.7 (2)116.4 (2)113.21 (15)115.6 (2)
C2—C1—N1—O1-178.0 (3)169.90 (17)-172.33 (18)169.11 (14)-174.6 (2)
A(O1/N1/C1)/B(C3-C8)82.8 (3)60.3 (2)56.6 (2)58.61 (10)50.10 (14)
A(O1/N1/C1)/C(C9-C14)39.7 (3)35.2 (2)44.6 (2)30.13 (11)73.37 (11)
B(C3-C8)/C(C9-C14)72.30 (18)81.43 (13)76.07 (12)75.30 (9)89.19 (6)
 

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