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In the title compound, C15H15N5O3S, two parallel inter­molecular N—H...S hydrogen bonds, forming an eight-membered ring, link two mol­ecules into a dimer unit; these dimer units linked into a chain of edge-fused rings by weak C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106041151/hj3022sup1.cif
Contains datablocks V, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106041151/hj3022Vsup2.hkl
Contains datablock V

CCDC reference: 628522

Comment top

The title compound, (V), has been obtained in the course of our study of the biological activity of the acylthiourea derivatives containing substituted pyrimidine. Many acylthiourea compounds show high herbicidal activity (Xue et al., 2004), and investigation of acylthioureas as herbicides has become the subject of intensive research (Xue & Wang, 2003; Xue et al., 2004; Xu et al., 2005). We have developed the synthesis of the title compoud, and report here its crystal structure.

The key feature of (V) is the two aromatic rings, namely a pyridine ring (C7–C11/N5) and a pyrimidine ring (C1—C4/N1/N2) with two ethoxy substituents (Fig. 1). The dihedral angle between the pyridine and pyrimidine ring planes is 78.3 (1)°. Instead of the catenarian structure usual in acylthiourea compounds, the acylthiourea bridge in the title compoud is embedded in a six-membered ring. The members of the ring are almost coplanar, and the dihedral angle between this plane and that of the pyridine ring is 3.5 (7)°, while the dihedral angle between the plane and that of the pyrimidine ring is 79.5 (0)°.

In (V), the molecules are linked by two parallel independent N—H···S hydrogen bonds (Table 2). Atom N4 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom S1 in the molecule at (1 − x, −y, 1 − z), linking the two molecules into a dimer unit, so generating a centrosymmetric R22(8) (Bernstein et al., 1995) ring centred at (1/2, 0, 1/2) (Fig. 2). In the dimer, the two pyridine rings are parallel, with a distance between their planes of 0.16 (1) Å, and the pyrimidine rings are also parallel, with a separation of 6.48 (7) Å. In addition, atom C15 in the molecule at (x, y, z) acts as a donor to atom O1 in the molecule at (−x, −y, 1 − z), generating a centrosymmetric R22(24) ring centred at (0, 0, 1/2). The combination of the R22(8) and R22(24) rings then generates a chain of edge-fused centrosymmetric rings.

Experimental top

3-carboxypyridine 1-oxide (13.9 g, 0.1 mol) was added to a 2% potassium hydroxide solution (200 ml) [solvent?] with stirring at room temperature and the mixture was stirred for 1 h. The precipitate was filtered off under suction and the filtrate was evaporated to dryness under vacuum. The product, potassium 1-oxidopyridine-3-carboxylate, (I), was dried under vacuum for another 1 h for further use. Excluding moisture, a solution of oxalyl dichloride (2.62 ml, 0.03 mol) in acetonitrile (5 ml) was added slowly to a stirred mixture of (I) (1.77 g, 0.01 mol) and acetonitrile (15 ml) at 273 K. The mixture was stirred for 1 h at 298 K and refluxed for another 1.5 h at 353 K. At the end of the reflux, the acetonitrile and the excess oxalyl dichloride were evaporated. To the residue, 3-(chlorocarbonyl)pyridine 1-oxide, (II), a solution of potassium thiocyanate in acetonitrile (20 ml) was added. The mixture was refluxed for 1 h at 353 K and then filtered off to yield a clear yellow solution of 3-(isothiocyanatocarbonyl)pyridine 1-oxide, (III). To the solution, 4,6-diethoxypyrimidin-2-amine (1.55 g, 0.01 mol) was added; the mixture was refluxed and stirred for another 6 h at 343 K, and then allowed to stand at room temperature for 10 h. The separated precipitate (V) was filtered off under suction and washed with 50% ethanol solution. The product was further purified by column chromatography on silica gel (hexane–ethyl acetate 8:1) to give a white solid. Crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation of a solution of (V) in hexane–ethyl acetate (6:1 v/v) at room temperature (m.p. 472–473 K). 1HNMR (DMSO-d6, 400 MHz): δ 1.32 (s, 3H, CH3), 4.25–4.34 (q, 2H, OCH2), 6.41 (s, 1H, py—H), 7.47—8.65 (m, 4H, pyridine-), 12.30 (s, 1H, NH); IR (KBr, cm−1): ν 3436 (N—H), 1740 (CO), 1254 (CS). Analysis calculated for C15H15N5O3S: C 52.16, H 4.38, N 20.28, O 13.90%; found: C 53.02, H 4.08, N 19.28, O 14.10%.

Refinement top

The ethyl group bonded to O3 was found to be disordered over two sites. The coordinates of the disordered components' C atoms were located in a difference Fourier map initially and refined with the occupancies tied to sum to unity. The site occupancies for the two components were refined freely to 0.672 (10) and 0.328 (10), respectively. The H atom bonded to the N atom was located in a difference Fourier map and refined isotropically. H atoms bonded to C atoms were positioned geometrically, with C—H distances in the range 0.93—0.97 Å and refined as riding with Uiso(H) values of 1.2 or 1.5 times Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (V), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level for non-H atoms and H atoms are shown as small spheres of arbitrary radii. The two sites shown for the ethyl bonded to O3 have occupancies of 0.672 (10) and 0.328 (10) respectively.
[Figure 2] Fig. 2. Part of the crystal structure of (V), showing the formation of a chain built from R22(8) and R22(24) rings. Only the major component of the disordered group is shown.
1-(4,6-diethoxypyrimidin-2-yl)-2-thioxo-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one top
Crystal data top
C15H15N5O3SF(000) = 720
Mr = 345.38Dx = 1.406 Mg m3
Monoclinic, P21/nMelting point: 473 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.0543 (10) ÅCell parameters from 923 reflections
b = 17.884 (2) Åθ = 2.3–20.1°
c = 10.3365 (12) ŵ = 0.22 mm1
β = 102.840 (2)°T = 298 K
V = 1631.9 (3) Å3Prism, colourless
Z = 40.10 × 0.09 × 0.07 mm
Data collection top
Bruker SMART CCD
diffractometer
2955 independent reflections
Radiation source: fine-focus sealed tube1651 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
ϕ and ω scansθmax = 25.3°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
Tmin = 0.989, Tmax = 0.994k = 1121
8352 measured reflectionsl = 1212
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 0.88 w = 1/[σ2(Fo2) + (0.0122P)2]
where P = (Fo2 + 2Fc2)/3
2955 reflections(Δ/σ)max < 0.001
232 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C15H15N5O3SV = 1631.9 (3) Å3
Mr = 345.38Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.0543 (10) ŵ = 0.22 mm1
b = 17.884 (2) ÅT = 298 K
c = 10.3365 (12) Å0.10 × 0.09 × 0.07 mm
β = 102.840 (2)°
Data collection top
Bruker SMART CCD
diffractometer
2955 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1651 reflections with I > 2σ(I)
Tmin = 0.989, Tmax = 0.994Rint = 0.069
8352 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 0.88Δρmax = 0.21 e Å3
2955 reflectionsΔρmin = 0.19 e Å3
232 parameters
Special details top

Experimental. n

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*/UeqOcc. (<1)
S10.38756 (9)0.05866 (4)0.32565 (8)0.0580 (3)
O10.4317 (2)0.10599 (12)0.7984 (2)0.0710 (7)
O20.2068 (2)0.31137 (12)0.05298 (19)0.0596 (6)
O30.1263 (3)0.11057 (13)0.0366 (2)0.0740 (7)
N10.0467 (3)0.13614 (13)0.2336 (2)0.0510 (7)
N20.2229 (2)0.23733 (13)0.2394 (2)0.0468 (7)
N30.2312 (2)0.16135 (12)0.4243 (2)0.0442 (6)
N40.3959 (3)0.08976 (14)0.5773 (2)0.0478 (7)
N50.0878 (3)0.25567 (13)0.4873 (2)0.0504 (7)
C10.1559 (4)0.25288 (17)0.1130 (3)0.0499 (8)
C20.0394 (3)0.21123 (17)0.0405 (3)0.0556 (9)
H20.00340.22220.04790.067*
C30.0111 (4)0.15243 (18)0.1049 (3)0.0543 (9)
C40.1614 (3)0.18010 (17)0.2873 (3)0.0467 (8)
C50.3361 (3)0.10550 (15)0.4473 (3)0.0458 (8)
C60.3696 (3)0.12651 (16)0.6879 (3)0.0471 (8)
C70.2644 (3)0.18871 (15)0.6569 (3)0.0415 (7)
C80.1935 (3)0.20324 (16)0.5260 (3)0.0422 (7)
C90.0577 (3)0.29812 (16)0.5834 (3)0.0569 (9)
H90.01430.33560.55940.068*
C100.1256 (3)0.29087 (17)0.7173 (3)0.0584 (9)
H100.10140.32300.78020.070*
C110.2298 (3)0.23440 (17)0.7535 (3)0.0518 (8)
H110.27640.22710.84230.062*
C120.3141 (4)0.36009 (18)0.1308 (3)0.0705 (10)
H12A0.40230.33220.17620.085*
H12B0.27030.38500.19680.085*
C130.3583 (3)0.41673 (18)0.0383 (3)0.0874 (12)
H13A0.40710.39180.02310.131*
H13B0.42670.45250.08870.131*
H13C0.26930.44200.00970.131*
C140.1748 (5)0.0486 (3)0.1039 (4)0.0997 (14)0.672 (10)
H14A0.08820.01960.14930.120*0.672 (10)
H14B0.22950.06600.16880.120*0.672 (10)
C150.2713 (9)0.0041 (4)0.0052 (6)0.112 (3)0.672 (10)
H15A0.30460.03890.04630.168*0.672 (10)
H15B0.21650.01170.05950.168*0.672 (10)
H15C0.35760.03310.03750.168*0.672 (10)
C14'0.1748 (5)0.0486 (3)0.1039 (4)0.0997 (14)0.328 (10)
H14C0.14500.05900.19820.120*0.328 (10)
H14D0.28470.04840.08080.120*0.328 (10)
C15'0.131 (2)0.0187 (8)0.0864 (16)0.106 (7)0.328 (10)
H15D0.17340.05280.13980.158*0.328 (10)
H15E0.02210.02110.11180.158*0.328 (10)
H15F0.16360.03210.00550.158*0.328 (10)
H40.468 (3)0.0501 (15)0.593 (3)0.083 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0806 (6)0.0500 (5)0.0463 (5)0.0165 (5)0.0201 (4)0.0033 (4)
O10.0913 (17)0.0747 (17)0.0391 (14)0.0197 (13)0.0020 (12)0.0095 (12)
O20.0812 (16)0.0569 (15)0.0409 (14)0.0082 (13)0.0136 (12)0.0133 (12)
O30.0961 (18)0.0707 (18)0.0484 (15)0.0163 (15)0.0016 (13)0.0021 (13)
N10.0658 (18)0.0502 (17)0.0359 (16)0.0028 (14)0.0088 (13)0.0010 (13)
N20.0612 (17)0.0443 (17)0.0361 (16)0.0097 (13)0.0132 (13)0.0066 (12)
N30.0554 (16)0.0423 (16)0.0334 (15)0.0107 (13)0.0071 (12)0.0055 (12)
N40.0591 (18)0.0424 (17)0.0396 (17)0.0119 (14)0.0062 (13)0.0056 (13)
N50.0578 (16)0.0522 (17)0.0410 (16)0.0108 (14)0.0103 (13)0.0027 (13)
C10.070 (2)0.046 (2)0.038 (2)0.0161 (18)0.0198 (17)0.0035 (17)
C20.076 (2)0.060 (2)0.0281 (18)0.0107 (19)0.0052 (17)0.0018 (17)
C30.066 (2)0.052 (2)0.043 (2)0.0029 (19)0.0089 (17)0.0093 (18)
C40.060 (2)0.045 (2)0.0367 (19)0.0163 (17)0.0123 (16)0.0016 (16)
C50.055 (2)0.0407 (19)0.042 (2)0.0027 (16)0.0113 (16)0.0038 (16)
C60.056 (2)0.045 (2)0.0386 (19)0.0008 (16)0.0061 (16)0.0029 (16)
C70.0487 (19)0.0433 (19)0.0318 (18)0.0019 (15)0.0078 (14)0.0013 (15)
C80.0460 (19)0.044 (2)0.0390 (19)0.0012 (15)0.0137 (15)0.0014 (15)
C90.066 (2)0.055 (2)0.049 (2)0.0174 (17)0.0112 (18)0.0010 (18)
C100.071 (2)0.062 (2)0.043 (2)0.0085 (19)0.0140 (17)0.0110 (17)
C110.060 (2)0.056 (2)0.0389 (19)0.0007 (18)0.0101 (16)0.0013 (16)
C120.089 (3)0.057 (2)0.069 (3)0.011 (2)0.026 (2)0.017 (2)
C130.097 (3)0.076 (3)0.094 (3)0.009 (2)0.033 (2)0.021 (2)
C140.120 (4)0.093 (4)0.077 (3)0.033 (3)0.003 (3)0.013 (3)
C150.109 (6)0.126 (6)0.083 (5)0.056 (5)0.018 (4)0.007 (4)
C14'0.120 (4)0.093 (4)0.077 (3)0.033 (3)0.003 (3)0.013 (3)
C15'0.145 (16)0.091 (11)0.098 (14)0.021 (10)0.065 (13)0.003 (9)
Geometric parameters (Å, º) top
S1—C51.661 (3)C7—C111.379 (3)
O1—C61.213 (3)C7—C81.387 (3)
O2—C11.349 (3)C9—C101.390 (3)
O2—C121.415 (3)C9—H90.9300
O3—C31.348 (3)C10—C111.376 (3)
O3—C141.429 (4)C10—H100.9300
N1—C41.323 (3)C11—H110.9300
N1—C31.349 (3)C12—C131.507 (4)
N2—C41.314 (3)C12—H12A0.9700
N2—C11.341 (3)C12—H12B0.9700
N3—C51.362 (3)C13—H13A0.9600
N3—C81.394 (3)C13—H13B0.9600
N3—C41.456 (3)C13—H13C0.9600
N4—C51.362 (3)C14—C151.428 (6)
N4—C61.384 (3)C14—H14A0.9700
N4—H40.95 (3)C14—H14B0.9700
N5—C91.326 (3)C15—H15A0.9600
N5—C81.336 (3)C15—H15B0.9600
C1—C21.371 (4)C15—H15C0.9600
C2—C31.376 (4)C15'—H15D0.9600
C2—H20.9300C15'—H15E0.9600
C6—C71.453 (3)C15'—H15F0.9600
C1—O2—C12118.5 (2)N5—C9—H9117.5
C3—O3—C14117.5 (3)C10—C9—H9117.5
C4—N1—C3112.5 (3)C11—C10—C9117.6 (3)
C4—N2—C1113.0 (3)C11—C10—H10121.2
C5—N3—C8122.8 (2)C9—C10—H10121.2
C5—N3—C4118.3 (2)C10—C11—C7119.4 (3)
C8—N3—C4118.9 (2)C10—C11—H11120.3
C5—N4—C6127.8 (3)C7—C11—H11120.3
C5—N4—H4115.5 (18)O2—C12—C13107.4 (3)
C6—N4—H4116.6 (18)O2—C12—H12A110.2
C9—N5—C8115.5 (2)C13—C12—H12A110.2
N2—C1—O2118.8 (3)O2—C12—H12B110.2
N2—C1—C2123.1 (3)C13—C12—H12B110.2
O2—C1—C2118.0 (3)H12A—C12—H12B108.5
C1—C2—C3116.7 (3)C12—C13—H13A109.5
C1—C2—H2121.7C12—C13—H13B109.5
C3—C2—H2121.7H13A—C13—H13B109.5
O3—C3—N1118.8 (3)C12—C13—H13C109.5
O3—C3—C2118.2 (3)H13A—C13—H13C109.5
N1—C3—C2123.0 (3)H13B—C13—H13C109.5
N2—C4—N1131.6 (3)C15—C14—O3106.8 (4)
N2—C4—N3114.7 (3)C15—C14—H14A110.4
N1—C4—N3113.7 (3)O3—C14—H14A110.4
N3—C5—N4115.6 (3)C15—C14—H14B110.4
N3—C5—S1122.7 (2)O3—C14—H14B110.4
N4—C5—S1121.7 (2)H14A—C14—H14B108.6
O1—C6—N4120.4 (3)C14—C15—H15A109.5
O1—C6—C7125.7 (3)C14—C15—H15B109.5
N4—C6—C7114.0 (3)H15A—C15—H15B109.5
C11—C7—C8117.7 (3)C14—C15—H15C109.5
C11—C7—C6122.5 (3)H15A—C15—H15C109.5
C8—C7—C6119.8 (3)H15B—C15—H15C109.5
N5—C8—C7124.7 (3)H15D—C15'—H15E109.5
N5—C8—N3115.5 (3)H15D—C15'—H15F109.5
C7—C8—N3119.8 (3)H15E—C15'—H15F109.5
N5—C9—C10125.0 (3)
C4—N2—C1—O2178.8 (2)C6—N4—C5—S1176.3 (2)
C4—N2—C1—C22.5 (4)C5—N4—C6—O1179.9 (3)
C12—O2—C1—N28.7 (4)C5—N4—C6—C70.3 (4)
C12—O2—C1—C2172.5 (3)O1—C6—C7—C113.5 (5)
N2—C1—C2—C31.9 (5)N4—C6—C7—C11176.7 (3)
O2—C1—C2—C3179.3 (3)O1—C6—C7—C8175.7 (3)
C14—O3—C3—N13.2 (5)N4—C6—C7—C84.1 (4)
C14—O3—C3—C2178.5 (3)C9—N5—C8—C73.7 (4)
C4—N1—C3—O3178.2 (2)C9—N5—C8—N3176.6 (3)
C4—N1—C3—C23.5 (4)C11—C7—C8—N53.9 (4)
C1—C2—C3—O3179.6 (3)C6—C7—C8—N5175.4 (3)
C1—C2—C3—N11.3 (5)C11—C7—C8—N3176.3 (2)
C1—N2—C4—N10.2 (5)C6—C7—C8—N34.4 (4)
C1—N2—C4—N3179.9 (2)C5—N3—C8—N5179.6 (2)
C3—N1—C4—N23.1 (5)C4—N3—C8—N53.5 (4)
C3—N1—C4—N3177.0 (2)C5—N3—C8—C70.2 (4)
C5—N3—C4—N297.3 (3)C4—N3—C8—C7176.8 (3)
C8—N3—C4—N279.8 (3)C8—N5—C9—C101.0 (5)
C5—N3—C4—N182.8 (3)N5—C9—C10—C111.3 (5)
C8—N3—C4—N1100.1 (3)C9—C10—C11—C71.1 (4)
C8—N3—C5—N43.9 (4)C8—C7—C11—C101.3 (4)
C4—N3—C5—N4179.1 (3)C6—C7—C11—C10178.0 (3)
C8—N3—C5—S1176.7 (2)C1—O2—C12—C13176.4 (2)
C4—N3—C5—S10.3 (4)C3—O3—C14—C15167.3 (5)
C6—N4—C5—N34.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···S1i0.95 (3)2.39 (3)3.320 (3)165 (2)
C15—H15A···O1ii0.962.483.379 (6)156
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC15H15N5O3S
Mr345.38
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)9.0543 (10), 17.884 (2), 10.3365 (12)
β (°) 102.840 (2)
V3)1631.9 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.10 × 0.09 × 0.07
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.989, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
8352, 2955, 1651
Rint0.069
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.081, 0.88
No. of reflections2955
No. of parameters232
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) top
S1—C51.661 (3)N3—C41.456 (3)
O1—C61.213 (3)N4—C51.362 (3)
N3—C51.362 (3)N4—C61.384 (3)
N3—C81.394 (3)C6—C71.453 (3)
C1—O2—C12118.5 (2)N4—C5—S1121.7 (2)
C3—O3—C14117.5 (3)O1—C6—N4120.4 (3)
C5—N4—C6127.8 (3)O1—C6—C7125.7 (3)
N3—C5—N4115.6 (3)N4—C6—C7114.0 (3)
C5—N3—C4—N297.3 (3)N4—C6—C7—C11176.7 (3)
C8—N3—C4—N279.8 (3)O1—C6—C7—C8175.7 (3)
C5—N3—C4—N182.8 (3)N4—C6—C7—C84.1 (4)
C8—N3—C4—N1100.1 (3)C9—N5—C8—C73.7 (4)
O1—C6—C7—C113.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···S1i0.95 (3)2.39 (3)3.320 (3)165 (2)
C15—H15A···O1ii0.962.483.379 (6)155.6
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1.
 

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