Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022271/wn2138sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022271/wn2138Isup2.hkl |
CCDC reference: 651434
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
For related literature, see: Fanni et al. (2000); Yi et al. (2004); Zhang et al. (2005).
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.
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).
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).
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.
Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. |
C16H11N3 | Z = 2 |
Mr = 245.28 | F(000) = 256 |
Triclinic, P1 | Dx = 1.373 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5580 (17) Å | Cell parameters from 1267 reflections |
b = 8.9289 (18) Å | θ = 2.5–27.9° |
c = 9.0170 (18) Å | µ = 0.08 mm−1 |
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 |
Rigaku R-AXIS RAPID-S diffractometer | 2053 independent reflections |
Radiation source: fine-focus sealed tube | 1624 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.982, Tmax = 0.985 | k = −10→10 |
4470 measured reflections | l = −10→10 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C16H11N3 | γ = 77.80 (3)° |
Mr = 245.28 | V = 593.2 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5580 (17) Å | Mo Kα radiation |
b = 8.9289 (18) Å | µ = 0.08 mm−1 |
c = 9.0170 (18) Å | T = 293 K |
α = 63.57 (3)° | 0.22 × 0.20 × 0.18 mm |
β = 75.43 (3)° |
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 = 0.985 | Rint = 0.038 |
4470 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.18 e Å−3 |
2053 reflections | Δρmin = −0.26 e Å−3 |
172 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.0212 (3) | 0.3020 (3) | 0.2577 (3) | 0.0213 (5) | |
C2 | 1.0449 (3) | 0.3347 (3) | 0.3913 (3) | 0.0231 (5) | |
H2 | 0.9621 | 0.3212 | 0.4842 | 0.028* | |
C3 | 1.1863 (3) | 0.3850 (3) | 0.3850 (3) | 0.0264 (6) | |
H3 | 1.1994 | 0.4054 | 0.4735 | 0.032* | |
C4 | 1.3144 (3) | 0.4070 (3) | 0.2444 (3) | 0.0277 (6) | |
H4 | 1.4107 | 0.4414 | 0.2416 | 0.033* | |
C5 | 1.2974 (3) | 0.3781 (3) | 0.1144 (3) | 0.0255 (6) | |
H5 | 1.3825 | 0.3924 | 0.0234 | 0.031* | |
C6 | 1.1504 (3) | 0.3258 (3) | 0.1153 (3) | 0.0217 (5) | |
C7 | 1.1293 (3) | 0.2950 (3) | −0.0173 (3) | 0.0241 (5) | |
H7 | 1.2129 | 0.3116 | −0.1099 | 0.029* | |
C8 | 0.9887 (3) | 0.2407 (3) | −0.0157 (3) | 0.0219 (5) | |
C9 | 0.9710 (3) | 0.2043 (3) | −0.1493 (3) | 0.0261 (6) | |
H9 | 1.0550 | 0.2197 | −0.2414 | 0.031* | |
C10 | 0.8342 (3) | 0.1479 (3) | −0.1439 (3) | 0.0295 (6) | |
H10 | 0.8254 | 0.1238 | −0.2316 | 0.035* | |
C11 | 0.7041 (3) | 0.1252 (3) | −0.0056 (3) | 0.0291 (6) | |
H11 | 0.6101 | 0.0873 | −0.0040 | 0.035* | |
C12 | 0.7148 (3) | 0.1578 (3) | 0.1245 (3) | 0.0269 (6) | |
H12 | 0.6280 | 0.1425 | 0.2139 | 0.032* | |
C13 | 0.8576 (3) | 0.2153 (3) | 0.1259 (3) | 0.0223 (5) | |
C14 | 0.8790 (3) | 0.2467 (3) | 0.2583 (3) | 0.0214 (5) | |
C15 | 0.6928 (3) | 0.0793 (3) | 0.5191 (3) | 0.0285 (6) | |
H15 | 0.7345 | −0.0271 | 0.5230 | 0.034* | |
C16 | 0.5572 (3) | 0.2780 (3) | 0.5699 (3) | 0.0286 (6) | |
H16 | 0.4792 | 0.3366 | 0.6233 | 0.034* | |
N1 | 0.7494 (2) | 0.2221 (2) | 0.4010 (2) | 0.0225 (5) | |
N2 | 0.6607 (2) | 0.3560 (2) | 0.4323 (2) | 0.0268 (5) | |
N3 | 0.5709 (2) | 0.1080 (3) | 0.6291 (2) | 0.0325 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0227 (12) | 0.0143 (12) | 0.0235 (12) | 0.0016 (9) | −0.0051 (10) | −0.0059 (10) |
C2 | 0.0252 (13) | 0.0223 (13) | 0.0213 (12) | −0.0023 (10) | −0.0015 (10) | −0.0102 (10) |
C3 | 0.0298 (13) | 0.0257 (14) | 0.0269 (13) | −0.0013 (10) | −0.0082 (10) | −0.0130 (11) |
C4 | 0.0237 (13) | 0.0267 (14) | 0.0326 (13) | −0.0069 (10) | −0.0063 (10) | −0.0098 (11) |
C5 | 0.0222 (13) | 0.0244 (13) | 0.0252 (12) | −0.0027 (10) | −0.0013 (10) | −0.0079 (11) |
C6 | 0.0224 (12) | 0.0176 (12) | 0.0222 (12) | 0.0023 (9) | −0.0056 (10) | −0.0069 (10) |
C7 | 0.0226 (12) | 0.0241 (13) | 0.0222 (12) | −0.0009 (10) | −0.0002 (10) | −0.0093 (10) |
C8 | 0.0231 (12) | 0.0195 (12) | 0.0209 (12) | 0.0005 (10) | −0.0058 (10) | −0.0068 (10) |
C9 | 0.0319 (14) | 0.0235 (13) | 0.0206 (12) | 0.0011 (10) | −0.0054 (10) | −0.0088 (10) |
C10 | 0.0418 (15) | 0.0244 (14) | 0.0262 (13) | −0.0026 (11) | −0.0123 (11) | −0.0111 (11) |
C11 | 0.0322 (14) | 0.0256 (14) | 0.0330 (14) | −0.0051 (11) | −0.0128 (11) | −0.0107 (11) |
C12 | 0.0243 (13) | 0.0259 (14) | 0.0298 (13) | −0.0027 (10) | −0.0036 (10) | −0.0116 (11) |
C13 | 0.0224 (12) | 0.0190 (12) | 0.0237 (12) | 0.0008 (10) | −0.0049 (10) | −0.0083 (10) |
C14 | 0.0199 (12) | 0.0185 (12) | 0.0221 (12) | −0.0013 (9) | 0.0005 (10) | −0.0079 (10) |
C15 | 0.0292 (14) | 0.0281 (14) | 0.0276 (13) | −0.0074 (11) | −0.0010 (11) | −0.0114 (11) |
C16 | 0.0226 (13) | 0.0386 (16) | 0.0271 (13) | −0.0038 (11) | −0.0012 (10) | −0.0172 (12) |
N1 | 0.0213 (10) | 0.0253 (11) | 0.0227 (10) | −0.0040 (8) | 0.0003 (8) | −0.0131 (9) |
N2 | 0.0220 (11) | 0.0320 (12) | 0.0291 (11) | −0.0005 (9) | −0.0001 (9) | −0.0186 (10) |
N3 | 0.0313 (12) | 0.0346 (13) | 0.0300 (12) | −0.0086 (9) | −0.0001 (9) | −0.0128 (10) |
C1—C14 | 1.405 (3) | C9—H9 | 0.9300 |
C1—C2 | 1.428 (3) | C10—C11 | 1.417 (3) |
C1—C6 | 1.435 (3) | C10—H10 | 0.9300 |
C2—C3 | 1.357 (3) | C11—C12 | 1.356 (3) |
C2—H2 | 0.9300 | C11—H11 | 0.9300 |
C3—C4 | 1.420 (3) | C12—C13 | 1.427 (3) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.354 (3) | C13—C14 | 1.402 (3) |
C4—H4 | 0.9300 | C14—N1 | 1.437 (3) |
C5—C6 | 1.429 (3) | C15—N3 | 1.315 (3) |
C5—H5 | 0.9300 | C15—N1 | 1.336 (3) |
C6—C7 | 1.399 (3) | C15—H15 | 0.9300 |
C7—C8 | 1.384 (3) | C16—N2 | 1.322 (3) |
C7—H7 | 0.9300 | C16—N3 | 1.356 (3) |
C8—C9 | 1.429 (3) | C16—H16 | 0.9300 |
C8—C13 | 1.438 (3) | N1—N2 | 1.377 (3) |
C9—C10 | 1.351 (3) | ||
C14—C1—C2 | 123.7 (2) | C9—C10—C11 | 120.5 (2) |
C14—C1—C6 | 118.1 (2) | C9—C10—H10 | 119.8 |
C2—C1—C6 | 118.2 (2) | C11—C10—H10 | 119.8 |
C3—C2—C1 | 121.0 (2) | C12—C11—C10 | 120.8 (2) |
C3—C2—H2 | 119.5 | C12—C11—H11 | 119.6 |
C1—C2—H2 | 119.5 | C10—C11—H11 | 119.6 |
C2—C3—C4 | 120.6 (2) | C11—C12—C13 | 120.9 (2) |
C2—C3—H3 | 119.7 | C11—C12—H12 | 119.5 |
C4—C3—H3 | 119.7 | C13—C12—H12 | 119.5 |
C5—C4—C3 | 120.5 (2) | C14—C13—C12 | 123.9 (2) |
C5—C4—H4 | 119.7 | C14—C13—C8 | 117.8 (2) |
C3—C4—H4 | 119.7 | C12—C13—C8 | 118.2 (2) |
C4—C5—C6 | 120.8 (2) | C13—C14—C1 | 123.0 (2) |
C4—C5—H5 | 119.6 | C13—C14—N1 | 118.69 (19) |
C6—C5—H5 | 119.6 | C1—C14—N1 | 118.35 (19) |
C7—C6—C5 | 122.1 (2) | N3—C15—N1 | 111.6 (2) |
C7—C6—C1 | 119.1 (2) | N3—C15—H15 | 124.2 |
C5—C6—C1 | 118.8 (2) | N1—C15—H15 | 124.2 |
C8—C7—C6 | 122.4 (2) | N2—C16—N3 | 116.3 (2) |
C8—C7—H7 | 118.8 | N2—C16—H16 | 121.8 |
C6—C7—H7 | 118.8 | N3—C16—H16 | 121.8 |
C7—C8—C9 | 121.8 (2) | C15—N1—N2 | 109.22 (18) |
C7—C8—C13 | 119.6 (2) | C15—N1—C14 | 129.43 (19) |
C9—C8—C13 | 118.6 (2) | N2—N1—C14 | 121.35 (17) |
C10—C9—C8 | 121.0 (2) | C16—N2—N1 | 101.12 (19) |
C10—C9—H9 | 119.5 | C15—N3—C16 | 101.70 (19) |
C8—C9—H9 | 119.5 | ||
C14—C1—C2—C3 | 178.8 (2) | C9—C8—C13—C14 | 178.1 (2) |
C6—C1—C2—C3 | −0.7 (3) | C7—C8—C13—C12 | −179.4 (2) |
C1—C2—C3—C4 | 0.2 (3) | C9—C8—C13—C12 | −1.1 (3) |
C2—C3—C4—C5 | 0.1 (4) | C12—C13—C14—C1 | 179.5 (2) |
C3—C4—C5—C6 | 0.3 (3) | C8—C13—C14—C1 | 0.3 (3) |
C4—C5—C6—C7 | 180.0 (2) | C12—C13—C14—N1 | −0.8 (3) |
C4—C5—C6—C1 | −0.9 (3) | C8—C13—C14—N1 | 179.99 (19) |
C14—C1—C6—C7 | 0.6 (3) | C2—C1—C14—C13 | 179.9 (2) |
C2—C1—C6—C7 | −179.8 (2) | C6—C1—C14—C13 | −0.5 (3) |
C14—C1—C6—C5 | −178.5 (2) | C2—C1—C14—N1 | 0.2 (3) |
C2—C1—C6—C5 | 1.1 (3) | C6—C1—C14—N1 | 179.79 (18) |
C5—C6—C7—C8 | 178.5 (2) | N3—C15—N1—N2 | −0.1 (3) |
C1—C6—C7—C8 | −0.6 (3) | N3—C15—N1—C14 | −179.2 (2) |
C6—C7—C8—C9 | −177.8 (2) | C13—C14—N1—C15 | 68.5 (3) |
C6—C7—C8—C13 | 0.4 (3) | C1—C14—N1—C15 | −111.7 (3) |
C7—C8—C9—C10 | 178.5 (2) | C13—C14—N1—N2 | −110.6 (2) |
C13—C8—C9—C10 | 0.3 (3) | C1—C14—N1—N2 | 69.2 (3) |
C8—C9—C10—C11 | 0.6 (3) | N3—C16—N2—N1 | −0.2 (3) |
C9—C10—C11—C12 | −0.7 (4) | C15—N1—N2—C16 | 0.1 (2) |
C10—C11—C12—C13 | −0.2 (4) | C14—N1—N2—C16 | 179.39 (19) |
C11—C12—C13—C14 | −178.0 (2) | N1—C15—N3—C16 | 0.0 (3) |
C11—C12—C13—C8 | 1.1 (3) | N2—C16—N3—C15 | 0.1 (3) |
C7—C8—C13—C14 | −0.2 (3) |
Experimental details
Crystal data | |
Chemical formula | C16H11N3 |
Mr | 245.28 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 593.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID-S |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.982, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4470, 2053, 1624 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.137, 1.12 |
No. of reflections | 2053 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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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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.