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The title compound, C16H11N3, was obtained by the reaction of 9-bromo­anthracene with 1,2,4-triazole in dimethyl­formamide. The mol­ecule is not planar; the triazole ring makes a dihedral angle of 68.7 (4)° with the anthracene plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022271/wn2138sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022271/wn2138Isup2.hkl
Contains datablock I

CCDC reference: 651434

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.062
  • wR factor = 0.137
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In the last few years it has been shown that 1,2,4-triazole and its derivatives are interesting building blocks for supramolecular systems. (Zhang et al., 2005; Yi et al. 2004; Fanni et al., 2000). Recently, we synthesized a new rigid triazole-ligand, namely 9-(1,2,4-triazol-1-yl)-anthracene, (I). Here we report the crystal structure of this ligand.

As shown in Fig. 1, the molecule of (I) is not planar; the triazole ring makes a dihedral angle of 68.7 (4)° with the anthracene plane. The C14—N1 bond distance is 1.437 (3) Å, whereas the C—N bond distances in the triazole ring range from 1.315 (3) to 1.356 (3) Å.

Related literature top

For related literature, see: Fanni et al. (2000); Yi et al. (2004); Zhang et al. (2005).

Experimental top

9-Bromoanthracene (1.29 g, 5.0 mmol), 1,2,4-triazole (0.35 g, 5.0 mmol), 1,10-phenanthroline (0.16 g, 0.88 mmol), anhydrous potassium carbonate (1.24 g, 9.0 mmol), and CuI (0.081 g, 0.043 mmol) were placed in a 50 ml flask with 30 ml dimethylformamide. The mixture was refluxed for 48 h under N2. After the reaction mixture was cooled to ambient temperature, dichloromethane was added to extract the brown sticky residue. The organic extracts were dried with anhydrous MgSO4 and further purified using a silica gel column (chloroform/ethyl acetate) to obtain a light yellow solid of 9-(1,2,4-triazol-1-yl)-anthracene (I) (yield: 0.49 g, 40%). The yellow powder was recrystallized from a mixture of chloroform and methanol (1:1), which gave single crystals suitable for X-ray diffraction.

Refinement top

The H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso(H) set equal to 1.2Ueq(C).

Structure description top

In the last few years it has been shown that 1,2,4-triazole and its derivatives are interesting building blocks for supramolecular systems. (Zhang et al., 2005; Yi et al. 2004; Fanni et al., 2000). Recently, we synthesized a new rigid triazole-ligand, namely 9-(1,2,4-triazol-1-yl)-anthracene, (I). Here we report the crystal structure of this ligand.

As shown in Fig. 1, the molecule of (I) is not planar; the triazole ring makes a dihedral angle of 68.7 (4)° with the anthracene plane. The C14—N1 bond distance is 1.437 (3) Å, whereas the C—N bond distances in the triazole ring range from 1.315 (3) to 1.356 (3) Å.

For related literature, see: Fanni et al. (2000); Yi et al. (2004); Zhang et al. (2005).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
9-(1,2,4-Triazol-1-yl)anthracene top
Crystal data top
C16H11N3Z = 2
Mr = 245.28F(000) = 256
Triclinic, P1Dx = 1.373 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5580 (17) ÅCell parameters from 1267 reflections
b = 8.9289 (18) Åθ = 2.5–27.9°
c = 9.0170 (18) ŵ = 0.08 mm1
α = 63.57 (3)°T = 293 K
β = 75.43 (3)°Block, colorless
γ = 77.80 (3)°0.22 × 0.20 × 0.18 mm
V = 593.2 (2) Å3
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
2053 independent reflections
Radiation source: fine-focus sealed tube1624 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.982, Tmax = 0.985k = 1010
4470 measured reflectionsl = 1010
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.1412P]
where P = (Fo2 + 2Fc2)/3
2053 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C16H11N3γ = 77.80 (3)°
Mr = 245.28V = 593.2 (2) Å3
Triclinic, P1Z = 2
a = 8.5580 (17) ÅMo Kα radiation
b = 8.9289 (18) ŵ = 0.08 mm1
c = 9.0170 (18) ÅT = 293 K
α = 63.57 (3)°0.22 × 0.20 × 0.18 mm
β = 75.43 (3)°
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
2053 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1624 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.985Rint = 0.038
4470 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.12Δρmax = 0.18 e Å3
2053 reflectionsΔρmin = 0.26 e Å3
172 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
C11.0212 (3)0.3020 (3)0.2577 (3)0.0213 (5)
C21.0449 (3)0.3347 (3)0.3913 (3)0.0231 (5)
H20.96210.32120.48420.028*
C31.1863 (3)0.3850 (3)0.3850 (3)0.0264 (6)
H31.19940.40540.47350.032*
C41.3144 (3)0.4070 (3)0.2444 (3)0.0277 (6)
H41.41070.44140.24160.033*
C51.2974 (3)0.3781 (3)0.1144 (3)0.0255 (6)
H51.38250.39240.02340.031*
C61.1504 (3)0.3258 (3)0.1153 (3)0.0217 (5)
C71.1293 (3)0.2950 (3)0.0173 (3)0.0241 (5)
H71.21290.31160.10990.029*
C80.9887 (3)0.2407 (3)0.0157 (3)0.0219 (5)
C90.9710 (3)0.2043 (3)0.1493 (3)0.0261 (6)
H91.05500.21970.24140.031*
C100.8342 (3)0.1479 (3)0.1439 (3)0.0295 (6)
H100.82540.12380.23160.035*
C110.7041 (3)0.1252 (3)0.0056 (3)0.0291 (6)
H110.61010.08730.00400.035*
C120.7148 (3)0.1578 (3)0.1245 (3)0.0269 (6)
H120.62800.14250.21390.032*
C130.8576 (3)0.2153 (3)0.1259 (3)0.0223 (5)
C140.8790 (3)0.2467 (3)0.2583 (3)0.0214 (5)
C150.6928 (3)0.0793 (3)0.5191 (3)0.0285 (6)
H150.73450.02710.52300.034*
C160.5572 (3)0.2780 (3)0.5699 (3)0.0286 (6)
H160.47920.33660.62330.034*
N10.7494 (2)0.2221 (2)0.4010 (2)0.0225 (5)
N20.6607 (2)0.3560 (2)0.4323 (2)0.0268 (5)
N30.5709 (2)0.1080 (3)0.6291 (2)0.0325 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0227 (12)0.0143 (12)0.0235 (12)0.0016 (9)0.0051 (10)0.0059 (10)
C20.0252 (13)0.0223 (13)0.0213 (12)0.0023 (10)0.0015 (10)0.0102 (10)
C30.0298 (13)0.0257 (14)0.0269 (13)0.0013 (10)0.0082 (10)0.0130 (11)
C40.0237 (13)0.0267 (14)0.0326 (13)0.0069 (10)0.0063 (10)0.0098 (11)
C50.0222 (13)0.0244 (13)0.0252 (12)0.0027 (10)0.0013 (10)0.0079 (11)
C60.0224 (12)0.0176 (12)0.0222 (12)0.0023 (9)0.0056 (10)0.0069 (10)
C70.0226 (12)0.0241 (13)0.0222 (12)0.0009 (10)0.0002 (10)0.0093 (10)
C80.0231 (12)0.0195 (12)0.0209 (12)0.0005 (10)0.0058 (10)0.0068 (10)
C90.0319 (14)0.0235 (13)0.0206 (12)0.0011 (10)0.0054 (10)0.0088 (10)
C100.0418 (15)0.0244 (14)0.0262 (13)0.0026 (11)0.0123 (11)0.0111 (11)
C110.0322 (14)0.0256 (14)0.0330 (14)0.0051 (11)0.0128 (11)0.0107 (11)
C120.0243 (13)0.0259 (14)0.0298 (13)0.0027 (10)0.0036 (10)0.0116 (11)
C130.0224 (12)0.0190 (12)0.0237 (12)0.0008 (10)0.0049 (10)0.0083 (10)
C140.0199 (12)0.0185 (12)0.0221 (12)0.0013 (9)0.0005 (10)0.0079 (10)
C150.0292 (14)0.0281 (14)0.0276 (13)0.0074 (11)0.0010 (11)0.0114 (11)
C160.0226 (13)0.0386 (16)0.0271 (13)0.0038 (11)0.0012 (10)0.0172 (12)
N10.0213 (10)0.0253 (11)0.0227 (10)0.0040 (8)0.0003 (8)0.0131 (9)
N20.0220 (11)0.0320 (12)0.0291 (11)0.0005 (9)0.0001 (9)0.0186 (10)
N30.0313 (12)0.0346 (13)0.0300 (12)0.0086 (9)0.0001 (9)0.0128 (10)
Geometric parameters (Å, º) top
C1—C141.405 (3)C9—H90.9300
C1—C21.428 (3)C10—C111.417 (3)
C1—C61.435 (3)C10—H100.9300
C2—C31.357 (3)C11—C121.356 (3)
C2—H20.9300C11—H110.9300
C3—C41.420 (3)C12—C131.427 (3)
C3—H30.9300C12—H120.9300
C4—C51.354 (3)C13—C141.402 (3)
C4—H40.9300C14—N11.437 (3)
C5—C61.429 (3)C15—N31.315 (3)
C5—H50.9300C15—N11.336 (3)
C6—C71.399 (3)C15—H150.9300
C7—C81.384 (3)C16—N21.322 (3)
C7—H70.9300C16—N31.356 (3)
C8—C91.429 (3)C16—H160.9300
C8—C131.438 (3)N1—N21.377 (3)
C9—C101.351 (3)
C14—C1—C2123.7 (2)C9—C10—C11120.5 (2)
C14—C1—C6118.1 (2)C9—C10—H10119.8
C2—C1—C6118.2 (2)C11—C10—H10119.8
C3—C2—C1121.0 (2)C12—C11—C10120.8 (2)
C3—C2—H2119.5C12—C11—H11119.6
C1—C2—H2119.5C10—C11—H11119.6
C2—C3—C4120.6 (2)C11—C12—C13120.9 (2)
C2—C3—H3119.7C11—C12—H12119.5
C4—C3—H3119.7C13—C12—H12119.5
C5—C4—C3120.5 (2)C14—C13—C12123.9 (2)
C5—C4—H4119.7C14—C13—C8117.8 (2)
C3—C4—H4119.7C12—C13—C8118.2 (2)
C4—C5—C6120.8 (2)C13—C14—C1123.0 (2)
C4—C5—H5119.6C13—C14—N1118.69 (19)
C6—C5—H5119.6C1—C14—N1118.35 (19)
C7—C6—C5122.1 (2)N3—C15—N1111.6 (2)
C7—C6—C1119.1 (2)N3—C15—H15124.2
C5—C6—C1118.8 (2)N1—C15—H15124.2
C8—C7—C6122.4 (2)N2—C16—N3116.3 (2)
C8—C7—H7118.8N2—C16—H16121.8
C6—C7—H7118.8N3—C16—H16121.8
C7—C8—C9121.8 (2)C15—N1—N2109.22 (18)
C7—C8—C13119.6 (2)C15—N1—C14129.43 (19)
C9—C8—C13118.6 (2)N2—N1—C14121.35 (17)
C10—C9—C8121.0 (2)C16—N2—N1101.12 (19)
C10—C9—H9119.5C15—N3—C16101.70 (19)
C8—C9—H9119.5
C14—C1—C2—C3178.8 (2)C9—C8—C13—C14178.1 (2)
C6—C1—C2—C30.7 (3)C7—C8—C13—C12179.4 (2)
C1—C2—C3—C40.2 (3)C9—C8—C13—C121.1 (3)
C2—C3—C4—C50.1 (4)C12—C13—C14—C1179.5 (2)
C3—C4—C5—C60.3 (3)C8—C13—C14—C10.3 (3)
C4—C5—C6—C7180.0 (2)C12—C13—C14—N10.8 (3)
C4—C5—C6—C10.9 (3)C8—C13—C14—N1179.99 (19)
C14—C1—C6—C70.6 (3)C2—C1—C14—C13179.9 (2)
C2—C1—C6—C7179.8 (2)C6—C1—C14—C130.5 (3)
C14—C1—C6—C5178.5 (2)C2—C1—C14—N10.2 (3)
C2—C1—C6—C51.1 (3)C6—C1—C14—N1179.79 (18)
C5—C6—C7—C8178.5 (2)N3—C15—N1—N20.1 (3)
C1—C6—C7—C80.6 (3)N3—C15—N1—C14179.2 (2)
C6—C7—C8—C9177.8 (2)C13—C14—N1—C1568.5 (3)
C6—C7—C8—C130.4 (3)C1—C14—N1—C15111.7 (3)
C7—C8—C9—C10178.5 (2)C13—C14—N1—N2110.6 (2)
C13—C8—C9—C100.3 (3)C1—C14—N1—N269.2 (3)
C8—C9—C10—C110.6 (3)N3—C16—N2—N10.2 (3)
C9—C10—C11—C120.7 (4)C15—N1—N2—C160.1 (2)
C10—C11—C12—C130.2 (4)C14—N1—N2—C16179.39 (19)
C11—C12—C13—C14178.0 (2)N1—C15—N3—C160.0 (3)
C11—C12—C13—C81.1 (3)N2—C16—N3—C150.1 (3)
C7—C8—C13—C140.2 (3)

Experimental details

Crystal data
Chemical formulaC16H11N3
Mr245.28
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.5580 (17), 8.9289 (18), 9.0170 (18)
α, β, γ (°)63.57 (3), 75.43 (3), 77.80 (3)
V3)593.2 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.22 × 0.20 × 0.18
Data collection
DiffractometerRigaku R-AXIS RAPID-S
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.982, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
4470, 2053, 1624
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.137, 1.12
No. of reflections2053
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.26

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

 

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