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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2375.
Published online 2008 November 20. doi:  10.1107/S1600536808037562
PMCID: PMC2959961

{5-Methyl-1-[8-(trifluoro­meth­yl)quinolin-4-yl]-1H-1,2,3-triazol-4-yl}(morpholino)methanone

Abstract

In the title mol­ecule, C18H16F3N5O2, the dihedral angle between the pyridine ring and the fused benzene ring is 4.50 (10)°. The triazole ring makes dihedral angles of 54.48 (12) and 57.91 (11)° with the pyridine and benzene rings, respectively. The morpholine ring atoms are disordered over two positions; the site-occupancy factors are ca 0.53 and 0.47. Inter­molecular C—H(...)F hydrogen bonding is found in the crystal structure. Furthermore, C—H(...)O and C—H(...)N intra­molecular contacts are also present.

Related literature

For the uses of 1,2,3-triazoles and their benzo derivatives, see: Sanghvi et al. (1990 [triangle]). For a related crystal structure, see: Thiruvalluvar et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2375-scheme1.jpg

Experimental

Crystal data

  • C18H16F3N5O2
  • M r = 391.36
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2375-efi1.jpg
  • a = 9.2836 (15) Å
  • b = 9.6164 (11) Å
  • c = 9.9272 (11) Å
  • α = 92.082 (9)°
  • β = 93.063 (11)°
  • γ = 105.728 (12)°
  • V = 850.7 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 200 (2) K
  • 0.53 × 0.28 × 0.22 mm

Data collection

  • Oxford Diffraction Gemini diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.934, T max = 0.973
  • 10917 measured reflections
  • 5503 independent reflections
  • 2919 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.077
  • wR(F 2) = 0.262
  • S = 1.02
  • 5503 reflections
  • 300 parameters
  • H-atom parameters constrained
  • Δρmax = 0.89 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037562/bq2106sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037562/bq2106Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007]. RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer.

supplementary crystallographic information

Comment

1,2,3-Triazoles and their benzo derivatives have attracted considerable attention because of their theoretical interest and synthetic value. They also find numerous applications in industry and agriculture due to their extensive biological activities and successful application as fluorescent whiteners, light stabilizers and optical brightening agents (Sanghvi et al., 1990). Thiruvalluvar et al. (2007) have reported the crystal structure of 1-{5-Methyl-1-[8-(trifluoromethyl)-quinolin-4-yl]-1H-1,2,3-triazol-4-yl}- ethanone.

In the title molecule, C18H16F3N5O2, Fig.1., the quinoline unit is nearly planar. The dihedral angle between the pyridine ring and the fused benzene ring is 4.50 (10)°. The triazole ring makes a dihedral angle of 54.48 (12)° and 57.91 (11)°, with that of pyridine and benzene rings, respectively. The trifluoromethyl group is coplanar with the attached benzene ring, except the fluoro atoms. The disordered morpholine ring is in chair form. Intermolecular C3—H3···F1(1 + x, y, z) hydrogen bond is found in the crystal structure. Further, C7—H7···F1, C16—H16B···O1, C23A—H23B···O1 and C25A—H25A···N13 intramolecular contacts are also found(Fig.2., Table 1).

Experimental

5-Methyl-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-1,2,3-triazole-4-carboxylic acid(10 g, 0.031 mol) was treated with thionyl chloride (3.7 g, 0.031 mol) in chlorofor (75 ml) and the mixture was heated to reflux for 2 h. The solvent was distilled out completely under vacuum. The residue was diluted with dry tetra hydrofuran (50 ml) and cooled to 273 K. This mixture was added slowly to the previously cooled morpholine in dry tetra hydrofuran (50 ml). Stirred for 1 h at 298 K and quenched to ice cooled water (500 ml). The precipitated solids were filtered, washed with water. The crude product was recrystallized from methanol. Yield 7.5 g (61.9%).

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 - 0.99 Å and Uiso(H) = 1.2 - 1.5 times Ueq(C). The morpholine ring atoms are disordered over two positions; the site-occupancy factors refined to 0.534 (5) and 0.466 (5).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. Only the major component is shown.
Fig. 2.
The packing of the title compound, viewed down the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted. Only the major component is shown.

Crystal data

C18H16F3N5O2Z = 2
Mr = 391.36F000 = 404
Triclinic, P1Dx = 1.528 Mg m3
Hall symbol: -P 1Melting point: 464.5 K
a = 9.2836 (15) ÅMo Kα radiation λ = 0.71073 Å
b = 9.6164 (11) ÅCell parameters from 4281 reflections
c = 9.9272 (11) Åθ = 4.8–32.7º
α = 92.082 (9)ºµ = 0.13 mm1
β = 93.063 (11)ºT = 200 (2) K
γ = 105.728 (12)ºNeedle, colourless
V = 850.7 (2) Å30.53 × 0.28 × 0.22 mm

Data collection

Oxford Diffraction Gemini diffractometer5503 independent reflections
Radiation source: fine-focus sealed tube2919 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.051
Detector resolution: 10.5081 pixels mm-1θmax = 32.6º
T = 200(2) Kθmin = 4.8º
[var phi] and ω scansh = −12→13
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2008)k = −14→13
Tmin = 0.934, Tmax = 0.973l = −14→14
10917 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.077H-atom parameters constrained
wR(F2) = 0.262  w = 1/[σ2(Fo2) + (0.1618P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5503 reflectionsΔρmax = 0.89 e Å3
300 parametersΔρmin = −0.48 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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 > 2σ(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*/UeqOcc. (<1)
F1−0.46264 (15)0.18931 (16)0.05088 (17)0.0495 (5)
F2−0.31631 (17)0.15031 (16)−0.09678 (13)0.0450 (5)
F3−0.31915 (17)0.05319 (14)0.09537 (15)0.0463 (5)
O10.5096 (2)0.69496 (19)0.61981 (17)0.0461 (6)
O210.8837 (3)1.1342 (2)0.5276 (2)0.0574 (7)
N1−0.0181 (2)0.18471 (18)0.03929 (19)0.0309 (5)
N110.3262 (2)0.52201 (19)0.23910 (18)0.0281 (5)
N120.4534 (2)0.5836 (2)0.17560 (19)0.0328 (5)
N130.5437 (2)0.6728 (2)0.2630 (2)0.0359 (6)
N24A0.6853 (5)0.8662 (4)0.5018 (4)0.0310 (10)0.534 (5)
C10.5494 (3)0.7483 (2)0.5121 (3)0.0458 (8)
C20.1246 (3)0.1857 (2)0.0423 (3)0.0377 (7)
C30.2428 (3)0.2962 (2)0.1060 (3)0.0353 (7)
C40.2085 (2)0.4121 (2)0.1684 (2)0.0254 (5)
C4A0.0590 (2)0.42273 (19)0.16018 (18)0.0215 (5)
C50.0162 (2)0.5470 (2)0.2076 (2)0.0267 (6)
C6−0.1308 (3)0.5473 (2)0.1979 (2)0.0306 (6)
C7−0.2428 (3)0.4259 (2)0.1427 (2)0.0302 (6)
C8−0.2055 (2)0.3047 (2)0.0935 (2)0.0271 (6)
C8A−0.0522 (2)0.3025 (2)0.09725 (19)0.0236 (5)
C140.4783 (3)0.6685 (2)0.3837 (2)0.0320 (6)
C150.3391 (3)0.5699 (2)0.3709 (2)0.0303 (6)
C160.2255 (3)0.5135 (3)0.4714 (2)0.0422 (8)
C18−0.3250 (3)0.1757 (2)0.0361 (2)0.0326 (6)
C22A0.8185 (12)1.0861 (9)0.6366 (10)0.047 (2)0.534 (5)
C23A0.7731 (6)0.9247 (5)0.6284 (4)0.0395 (16)0.534 (5)
C25A0.7564 (6)0.9318 (5)0.3820 (4)0.0370 (14)0.534 (5)
C26A0.8030 (12)1.0939 (9)0.4013 (10)0.046 (2)0.534 (5)
C23B0.6638 (6)0.9736 (6)0.6483 (5)0.0366 (16)0.466 (5)
N24B0.6066 (6)0.8915 (4)0.5195 (4)0.0328 (14)0.466 (5)
C22B0.8321 (12)1.0331 (9)0.6461 (12)0.046 (3)0.466 (5)
C25B0.6442 (6)0.9771 (5)0.4021 (5)0.0327 (14)0.466 (5)
C26B0.8137 (12)1.0426 (11)0.4118 (12)0.049 (3)0.466 (5)
H20.149070.10638−0.001560.0452*
H16B0.277100.507860.558910.0633*
H16C0.163590.416960.439980.0633*
H22A0.729041.122060.646100.0556*0.534 (5)
H22B0.888471.122240.716940.0556*0.534 (5)
H23A0.863880.889510.634960.0473*0.534 (5)
H23B0.712710.889080.705650.0473*0.534 (5)
H25A0.685070.902100.301720.0446*0.534 (5)
H25B0.845420.896910.366230.0446*0.534 (5)
H26A0.866681.136320.328110.0556*0.534 (5)
H26B0.713251.130770.397660.0556*0.534 (5)
H30.343510.290840.106010.0423*
H50.090320.629520.246020.0320*
H6−0.157910.630740.228820.0368*
H7−0.344880.427250.139260.0362*
H16A0.161610.578880.481000.0633*
H22C0.877220.951110.639220.0551*0.466 (5)
H22D0.871151.087950.732750.0551*0.466 (5)
H23C0.638970.909640.724550.0439*0.466 (5)
H23D0.616941.053880.660200.0439*0.466 (5)
H25C0.592501.054640.401050.0389*0.466 (5)
H25D0.612400.915130.318110.0389*0.466 (5)
H26C0.860560.961670.405980.0586*0.466 (5)
H26D0.839671.098990.330830.0586*0.466 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0213 (7)0.0542 (9)0.0675 (11)0.0026 (6)0.0085 (7)−0.0172 (8)
F20.0394 (8)0.0581 (9)0.0325 (7)0.0072 (7)0.0008 (6)−0.0138 (6)
F30.0431 (9)0.0326 (7)0.0543 (9)−0.0039 (6)−0.0011 (7)0.0018 (6)
O10.0593 (12)0.0418 (9)0.0343 (9)0.0112 (8)−0.0081 (8)−0.0002 (7)
O210.0619 (14)0.0487 (11)0.0546 (12)0.0067 (10)−0.0078 (11)−0.0056 (9)
N10.0293 (10)0.0270 (8)0.0373 (10)0.0100 (7)0.0030 (8)−0.0062 (7)
N110.0242 (9)0.0324 (8)0.0283 (8)0.0096 (7)0.0017 (7)−0.0047 (7)
N120.0233 (9)0.0377 (9)0.0363 (10)0.0067 (7)0.0048 (8)−0.0052 (8)
N130.0306 (10)0.0340 (9)0.0394 (11)0.0045 (8)−0.0031 (8)−0.0040 (8)
N24A0.035 (2)0.0281 (17)0.0241 (17)−0.0003 (15)0.0002 (16)−0.0037 (13)
C10.0709 (19)0.0238 (10)0.0342 (12)0.0035 (11)−0.0191 (12)−0.0020 (9)
C20.0310 (12)0.0310 (10)0.0527 (14)0.0135 (9)0.0012 (10)−0.0125 (9)
C30.0242 (10)0.0368 (11)0.0465 (13)0.0134 (9)−0.0006 (10)−0.0109 (9)
C40.0191 (9)0.0281 (9)0.0280 (10)0.0058 (7)0.0001 (8)−0.0031 (7)
C4A0.0184 (9)0.0226 (8)0.0224 (9)0.0037 (7)0.0057 (7)−0.0029 (7)
C50.0263 (10)0.0282 (9)0.0258 (10)0.0084 (8)0.0041 (8)−0.0063 (7)
C60.0296 (11)0.0333 (10)0.0320 (11)0.0132 (9)0.0081 (9)−0.0029 (8)
C70.0223 (10)0.0386 (11)0.0309 (11)0.0096 (8)0.0093 (8)−0.0038 (8)
C80.0240 (10)0.0307 (10)0.0262 (10)0.0063 (8)0.0063 (8)−0.0003 (7)
C8A0.0243 (10)0.0230 (8)0.0237 (9)0.0068 (7)0.0039 (8)−0.0019 (7)
C140.0374 (12)0.0269 (10)0.0320 (11)0.0114 (9)−0.0052 (9)−0.0015 (8)
C150.0350 (12)0.0339 (10)0.0250 (10)0.0153 (9)0.0003 (9)−0.0033 (8)
C160.0407 (14)0.0551 (14)0.0297 (11)0.0106 (11)0.0080 (10)−0.0019 (10)
C180.0264 (11)0.0381 (11)0.0326 (11)0.0079 (9)0.0068 (9)−0.0061 (9)
C22A0.047 (4)0.043 (4)0.044 (3)0.005 (3)−0.001 (3)−0.013 (4)
C23A0.043 (3)0.046 (3)0.024 (2)0.004 (2)−0.0029 (19)−0.0016 (17)
C25A0.038 (3)0.036 (2)0.031 (2)0.0001 (19)0.0040 (19)−0.0035 (17)
C26A0.049 (4)0.044 (4)0.041 (3)0.006 (3)−0.010 (3)0.006 (3)
C23B0.029 (3)0.047 (3)0.030 (2)0.005 (2)0.004 (2)−0.008 (2)
N24B0.037 (3)0.031 (2)0.026 (2)0.0027 (19)0.0019 (19)−0.0058 (15)
C22B0.041 (4)0.040 (5)0.049 (4)0.002 (4)−0.012 (3)−0.007 (4)
C25B0.030 (2)0.029 (2)0.036 (3)0.0027 (18)0.001 (2)0.0031 (18)
C26B0.042 (4)0.059 (7)0.047 (4)0.010 (4)0.017 (3)0.018 (5)

Geometric parameters (Å, °)

F1—C181.334 (3)C8—C8A1.428 (3)
F2—C181.344 (2)C14—C151.376 (3)
F3—C181.349 (2)C15—C161.498 (3)
O1—C11.234 (3)C22A—C23A1.492 (10)
O21—C22A1.306 (10)C22B—C23B1.513 (12)
O21—C26A1.411 (10)C25A—C26A1.503 (10)
O21—C22B1.565 (11)C25B—C26B1.525 (13)
O21—C26B1.434 (12)C2—H20.9500
N1—C21.321 (3)C3—H30.9500
N1—C8A1.371 (3)C5—H50.9500
N11—N121.368 (3)C6—H60.9500
N11—C41.429 (3)C7—H70.9500
N11—C151.359 (3)C16—H16A0.9800
N12—N131.292 (3)C16—H16B0.9800
N13—C141.369 (3)C16—H16C0.9800
N24A—C11.461 (5)C22A—H22A0.9900
N24A—C23A1.467 (6)C22A—H22B0.9900
N24A—C25A1.470 (6)C22B—H22D0.9900
N24B—C11.333 (4)C22B—H22C0.9900
N24B—C23B1.472 (6)C23A—H23B0.9900
N24B—C25B1.454 (6)C23A—H23A0.9900
C1—C141.488 (3)C23B—H23D0.9900
C2—C31.406 (3)C23B—H23C0.9900
C3—C41.375 (3)C25A—H25B0.9900
C4—C4A1.417 (3)C25A—H25A0.9900
C4A—C51.430 (3)C25B—H25D0.9900
C4A—C8A1.423 (3)C25B—H25C0.9900
C5—C61.364 (3)C26A—H26B0.9900
C6—C71.407 (3)C26A—H26A0.9900
C7—C81.383 (3)C26B—H26C0.9900
C8—C181.493 (3)C26B—H26D0.9900
F1···C3i3.237 (3)C4A···H16C2.9000
F1···N12ii3.179 (3)C5···H16A2.9300
F1···F3iii2.920 (2)C5···H16C3.0900
F2···C22Biv3.270 (12)C6···H16Bxi2.8300
F2···C23Biv2.965 (5)C7···H16Bxi3.0600
F2···N12.945 (3)C8···H26Av3.0300
F2···C22Aiv3.100 (10)C8A···H26Av2.8600
F3···C26Av3.157 (10)C14···H23Dviii3.0700
F3···F1iii2.920 (2)C14···H25A2.7100
F3···C25Bv3.172 (5)C14···H25D2.4900
F3···N12.832 (2)C15···H52.7700
F3···C25Av3.229 (4)C16···H52.9100
F3···C26Bv3.328 (12)C22A···H5viii2.8200
F1···H72.3700C22A···H25Bix3.0800
F1···H3i2.3500C22B···H26Cix2.9100
F2···H22Div2.6600C23B···H25Dviii3.0600
F2···H22Aiv2.6300C23B···H25Cviii2.3400
F2···H23Div2.5400C25B···H23Dviii2.4000
F2···H23Civ2.7900C25B···H25Cviii2.9800
F2···H22Biv2.7800C26A···H23Aix3.0900
F3···H26Av2.7700C26B···H22Cix2.9300
F3···H25Dv2.6400H2···F3vi2.6600
F3···H26Dv2.6500H2···N1vi2.7400
F3···H25Av2.5600H3···H23Bvii2.5700
F3···H2vi2.6600H3···F1x2.3500
O1···C163.012 (3)H3···N122.7700
O1···N11vii3.217 (3)H5···N112.6700
O1···C15vii3.227 (3)H5···H16A2.4900
O21···N24B2.963 (5)H5···C152.7700
O21···N24A2.726 (4)H5···C162.9100
O1···H23C2.2700H5···C22Aviii2.8200
O1···H23B2.3600H5···H22Bviii2.3600
O1···H25Cviii2.8300H6···N13i2.9400
O1···H16B2.4400H7···F12.3700
O21···H16Aviii2.9100H7···N12i2.7300
O21···H25Bix2.7700H16A···C52.9300
O21···H26Cix2.8300H16A···H52.4900
N1···F22.945 (3)H16A···O21viii2.9100
N1···F32.832 (2)H16B···C6xi2.8300
N11···O1vii3.217 (3)H16B···C7xi3.0600
N12···F1ii3.179 (3)H16B···C13.0000
N13···C25A2.893 (5)H16B···O12.4400
N13···C25B3.071 (5)H16C···C4A2.9000
N13···N24B3.168 (4)H16C···C53.0900
N13···N24A2.971 (4)H16C···C42.7500
N24A···N132.971 (4)H22A···H26B2.4700
N24A···O212.726 (4)H22A···F2xii2.6300
N24B···N24Bviii3.262 (7)H22B···H5viii2.3600
N24B···O212.963 (5)H22B···F2xii2.7800
N24B···N133.168 (4)H22C···H26C2.3200
N24B···C25Bviii3.056 (8)H22C···C26Bix2.9300
N1···H2vi2.7400H22C···H26Cix2.4200
N11···H52.6700H22D···F2xii2.6600
N12···H7x2.7300H23A···H26Aix2.5900
N12···H32.7700H23A···C26Aix3.0900
N13···H25A2.2500H23B···O12.3600
N13···H6x2.9400H23B···C2vii3.0600
N13···H25D2.2800H23B···H3vii2.5700
N24B···H23Dviii2.8300H23B···C3vii2.7200
N24B···H25Cviii2.2300H23C···O12.2700
C2···C6ii3.558 (3)H23C···F2xii2.7900
C3···F1x3.237 (3)H23C···C3vii3.0300
C3···C23Avii3.430 (5)H23C···H25Cviii2.5400
C4···C7ii3.500 (3)H23D···H25C2.5700
C4A···C163.355 (3)H23D···F2xii2.5400
C5···C8Aii3.395 (3)H23D···H25Dviii2.2500
C5···C153.280 (3)H23D···N24Bviii2.8300
C5···C163.255 (3)H23D···C25Bviii2.4000
C6···C16xi3.473 (3)H23D···C14viii3.0700
C6···C2ii3.558 (3)H23D···H25Cviii1.9900
C7···C4ii3.500 (3)H25A···N132.2500
C8A···C5ii3.395 (3)H25A···C142.7100
C15···C53.280 (3)H25A···F3xiii2.5600
C15···O1vii3.227 (3)H25B···C22Aix3.0800
C16···C53.255 (3)H25B···O21ix2.7700
C16···C6xi3.473 (3)H25C···O1viii2.8300
C16···O13.012 (3)H25C···H23D2.5700
C16···C4A3.355 (3)H25C···C25Bviii2.9800
C22A···F2xii3.100 (10)H25C···H23Cviii2.5400
C22B···F2xii3.270 (12)H25C···H23Dviii1.9900
C23A···C3vii3.430 (5)H25C···N24Bviii2.2300
C23B···F2xii2.965 (5)H25C···C23Bviii2.3400
C23B···C25Bviii3.041 (8)H25C···C1viii2.7300
C25A···F3xiii3.229 (4)H25D···F3xiii2.6400
C25A···N132.893 (5)H25D···N132.2800
C25B···N133.071 (5)H25D···H23Dviii2.2500
C25B···F3xiii3.172 (5)H25D···C142.4900
C25B···C23Bviii3.041 (8)H25D···C23Bviii3.0600
C25B···C25Bviii3.503 (8)H26A···C8xiii3.0300
C25B···N24Bviii3.056 (8)H26A···F3xiii2.7700
C26A···F3xiii3.157 (10)H26A···C8Axiii2.8600
C26B···F3xiii3.328 (12)H26A···H23Aix2.5900
C1···H25Cviii2.7300H26B···H22A2.4700
C1···H16B3.0000H26C···H22C2.3200
C2···H23Bvii3.0600H26C···O21ix2.8300
C3···H23Cvii3.0300H26C···C22Bix2.9100
C3···H23Bvii2.7200H26C···H22Cix2.4200
C4···H16C2.7500H26D···F3xiii2.6500
C22A—O21—C26A118.7 (6)N1—C2—H2118.00
C22B—O21—C26B101.9 (6)C3—C2—H2118.00
C2—N1—C8A117.59 (18)C2—C3—H3121.00
N12—N11—C4119.49 (17)C4—C3—H3121.00
N12—N11—C15111.24 (18)C4A—C5—H5120.00
C4—N11—C15129.00 (19)C6—C5—H5120.00
N11—N12—N13106.99 (17)C5—C6—H6119.00
N12—N13—C14109.29 (19)C7—C6—H6120.00
C1—N24A—C23A116.8 (3)C6—C7—H7120.00
C1—N24A—C25A130.2 (4)C8—C7—H7120.00
C23A—N24A—C25A112.9 (4)C15—C16—H16A109.00
C1—N24B—C23B122.3 (4)C15—C16—H16B109.00
C1—N24B—C25B123.6 (4)C15—C16—H16C109.00
C23B—N24B—C25B113.2 (4)H16A—C16—H16B109.00
N24A—C1—C14116.7 (3)H16A—C16—H16C109.00
N24B—C1—C14121.6 (3)H16B—C16—H16C110.00
O1—C1—C14118.48 (19)O21—C22A—H22A110.00
O1—C1—N24B114.9 (3)O21—C22A—H22B110.00
O1—C1—N24A123.2 (3)C23A—C22A—H22A110.00
N1—C2—C3124.4 (2)C23A—C22A—H22B110.00
C2—C3—C4118.1 (2)H22A—C22A—H22B108.00
C3—C4—C4A120.16 (19)O21—C22B—H22C109.00
N11—C4—C4A120.93 (17)O21—C22B—H22D109.00
N11—C4—C3118.90 (19)C23B—C22B—H22C109.00
C5—C4A—C8A119.32 (17)C23B—C22B—H22D109.00
C4—C4A—C8A116.74 (17)H22C—C22B—H22D108.00
C4—C4A—C5123.92 (17)H23A—C23A—H23B108.00
C4A—C5—C6120.15 (17)N24A—C23A—H23B109.00
C5—C6—C7121.0 (2)C22A—C23A—H23A109.00
C6—C7—C8120.5 (2)N24A—C23A—H23A109.00
C8A—C8—C18119.66 (18)C22A—C23A—H23B109.00
C7—C8—C8A120.05 (19)N24B—C23B—H23D110.00
C7—C8—C18120.3 (2)C22B—C23B—H23C110.00
N1—C8A—C4A122.68 (18)N24B—C23B—H23C110.00
N1—C8A—C8118.56 (17)H23C—C23B—H23D108.00
C4A—C8A—C8118.76 (17)C22B—C23B—H23D110.00
N13—C14—C1126.0 (2)N24A—C25A—H25B110.00
C1—C14—C15124.6 (2)N24A—C25A—H25A110.00
N13—C14—C15109.24 (18)H25A—C25A—H25B108.00
C14—C15—C16132.13 (19)C26A—C25A—H25A110.00
N11—C15—C16124.6 (2)C26A—C25A—H25B110.00
N11—C15—C14103.20 (19)N24B—C25B—H25D110.00
F1—C18—F2106.17 (19)H25C—C25B—H25D109.00
F1—C18—F3106.26 (18)C26B—C25B—H25C110.00
F1—C18—C8112.44 (17)C26B—C25B—H25D110.00
F3—C18—C8112.44 (19)N24B—C25B—H25C110.00
F2—C18—F3106.18 (16)O21—C26A—H26A110.00
F2—C18—C8112.84 (18)O21—C26A—H26B110.00
O21—C22A—C23A109.8 (7)C25A—C26A—H26A110.00
O21—C22B—C23B114.1 (7)C25A—C26A—H26B110.00
N24A—C23A—C22A111.7 (5)H26A—C26A—H26B108.00
N24B—C23B—C22B108.5 (6)O21—C26B—H26C107.00
N24A—C25A—C26A110.5 (5)O21—C26B—H26D107.00
N24B—C25B—C26B107.5 (6)C25B—C26B—H26C107.00
O21—C26A—C25A109.2 (6)C25B—C26B—H26D108.00
O21—C26B—C25B119.4 (8)H26C—C26B—H26D107.00
C26A—O21—C22A—C23A58.9 (10)C2—C3—C4—C4A−4.0 (3)
C22A—O21—C26A—C25A−58.4 (10)N11—C4—C4A—C56.7 (3)
C8A—N1—C2—C32.9 (4)N11—C4—C4A—C8A−175.01 (17)
C2—N1—C8A—C4A−0.5 (3)C3—C4—C4A—C5−172.2 (2)
C2—N1—C8A—C8179.1 (2)C3—C4—C4A—C8A6.1 (3)
C4—N11—N12—N13−176.69 (18)C4—C4A—C5—C6−178.86 (19)
C15—N11—N12—N13−2.2 (2)C8A—C4A—C5—C62.9 (3)
N12—N11—C4—C351.3 (3)C4—C4A—C8A—N1−3.9 (3)
N12—N11—C4—C4A−127.7 (2)C4—C4A—C8A—C8176.46 (17)
C15—N11—C4—C3−122.1 (3)C5—C4A—C8A—N1174.44 (18)
C15—N11—C4—C4A59.0 (3)C5—C4A—C8A—C8−5.2 (3)
N12—N11—C15—C142.4 (2)C4A—C5—C6—C70.6 (3)
N12—N11—C15—C16−174.1 (2)C5—C6—C7—C8−1.8 (3)
C4—N11—C15—C14176.2 (2)C6—C7—C8—C8A−0.6 (3)
C4—N11—C15—C16−0.4 (4)C6—C7—C8—C18179.48 (18)
N11—N12—N13—C141.1 (2)C7—C8—C8A—N1−175.58 (18)
N12—N13—C14—C1176.0 (2)C7—C8—C8A—C4A4.1 (3)
N12—N13—C14—C150.4 (3)C18—C8—C8A—N14.3 (3)
C23A—N24A—C1—O1−2.2 (5)C18—C8—C8A—C4A−176.01 (17)
C23A—N24A—C1—C14−167.5 (3)C7—C8—C18—F1−5.8 (3)
C25A—N24A—C1—O1173.2 (4)C7—C8—C18—F2114.3 (2)
C25A—N24A—C1—C147.9 (6)C7—C8—C18—F3−125.7 (2)
C1—N24A—C23A—C22A−134.2 (6)C8A—C8—C18—F1174.31 (17)
C25A—N24A—C23A—C22A49.7 (7)C8A—C8—C18—F2−65.7 (3)
C1—N24A—C25A—C26A135.5 (6)C8A—C8—C18—F354.4 (3)
C23A—N24A—C25A—C26A−49.0 (7)N13—C14—C15—N11−1.7 (2)
O1—C1—C14—N13−150.7 (2)N13—C14—C15—C16174.5 (2)
O1—C1—C14—C1524.3 (4)C1—C14—C15—N11−177.3 (2)
N24A—C1—C14—N1315.3 (4)C1—C14—C15—C16−1.2 (4)
N24A—C1—C14—C15−169.7 (3)O21—C22A—C23A—N24A−52.0 (9)
N1—C2—C3—C4−0.7 (4)N24A—C25A—C26A—O2149.3 (9)
C2—C3—C4—N11177.1 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z; (iii) −x−1, −y, −z; (iv) x−1, y−1, z−1; (v) x−1, y−1, z; (vi) −x, −y, −z; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y+2, −z+1; (ix) −x+2, −y+2, −z+1; (x) x+1, y, z; (xi) −x, −y+1, −z+1; (xii) x+1, y+1, z+1; (xiii) x+1, y+1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···F1x0.952.353.237 (3)156
C7—H7···F10.952.372.703 (3)100
C16—H16B···O10.982.443.012 (3)117
C23A—H23B···O10.992.362.812 (5)107
C25A—H25A···N130.992.252.893 (5)122

Symmetry codes: (x) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2106).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
  • Sanghvi, Y. S., Bhattacharya, B. K., Kini, G. D., Matsumoto, S. S., Larson, S. B., Jolley, W. B., Robins, R. K. & Revankar, G. R. (1990). J. Med. Chem.33, 336–344. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Thiruvalluvar, A., Subramanyam, M., Butcher, R. J. & Mahalinga, M. (2007). Acta Cryst. E63, o4813–o4814.

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