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The title compound, C
24H
14N
2, is a rigid-rod terminal dialkyne exhibiting extended π-conjugation through the heteroaromatic linker unit in the backbone. There is an intermolecular C—H
N close contact between one of the terminal alkyne groups and one of the N atoms, with a C
N distance of 3.374 (3) Å. Intermolecular interactions are also present between the alkynyl H atoms and C
C groups.
Supporting information
CCDC reference: 200772
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.081
- Data-to-parameter ratio = 7.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(4) - C(41) = 1.44 Ang.
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(7) - C(71) = 1.44 Ang.
PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 54
C5 -C4 -C41 -C42 -16.00 5.00 1.555 1.555 1.555 1.555
PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 55
C3 -C4 -C41 -C42 163.00 5.00 1.555 1.555 1.555 1.555
PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 56
C6 -C7 -C71 -C72 -18.00 6.00 1.555 1.555 1.555 1.555
PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 57
C8 -C7 -C71 -C72 161.00 6.00 1.555 1.555 1.555 1.555
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 25.06
From the CIF: _reflns_number_total 1654
Count of symmetry unique reflns 1678
Completeness (_total/calc) 98.57%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
6 Alert Level C = Please check
Data collection: COLLECT (Nonius, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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).
Crystal data top
C24H14N2 | F(000) = 344 |
Mr = 330.37 | Dx = 1.279 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.870 (3) Å | Cell parameters from 3933 reflections |
b = 5.8527 (9) Å | θ = 2.9–25.0° |
c = 14.888 (3) Å | µ = 0.08 mm−1 |
β = 93.924 (9)° | T = 170 K |
V = 858.0 (3) Å3 | Plate, colourless |
Z = 2 | 0.23 × 0.09 × 0.04 mm |
Data collection top
Nonius KappaCCD diffractometer | Rint = 0.025 |
107 two degree scans | θmax = 25.1°, θmin = 4.1° |
2838 measured reflections | h = −11→11 |
1654 independent reflections | k = −6→5 |
1400 reflections with I > 2σ(I) | l = −17→17 |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.0338P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max < 0.001 |
wR(F2) = 0.081 | Δρmax = 0.16 e Å−3 |
S = 1.05 | Δρmin = −0.15 e Å−3 |
1654 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
236 parameters | Extinction coefficient: 0.041 (5) |
244 restraints | Absolute structure: see text |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.66011 (19) | 0.8312 (3) | 0.31290 (12) | 0.0271 (4) | |
N2 | 0.52857 (18) | 0.5722 (3) | 0.17370 (11) | 0.0257 (4) | |
C1 | 0.5332 (2) | 0.8757 (3) | 0.28383 (14) | 0.0254 (5) | |
C2 | 0.4680 (2) | 0.7478 (3) | 0.21023 (14) | 0.0246 (5) | |
C3 | 0.6576 (2) | 0.5198 (4) | 0.20653 (14) | 0.0244 (5) | |
C4 | 0.7244 (2) | 0.3250 (4) | 0.17174 (15) | 0.0279 (5) | |
C5 | 0.8524 (2) | 0.2697 (4) | 0.20802 (15) | 0.0341 (6) | |
H5 | 0.8963 | 0.1374 | 0.1871 | 0.041* | |
C6 | 0.9190 (2) | 0.4038 (4) | 0.27485 (16) | 0.0361 (6) | |
H6 | 1.0075 | 0.3616 | 0.298 | 0.043* | |
C7 | 0.8590 (2) | 0.5965 (4) | 0.30817 (15) | 0.0297 (5) | |
C8 | 0.7244 (2) | 0.6538 (4) | 0.27424 (14) | 0.0264 (5) | |
C11 | 0.4650 (2) | 1.0585 (4) | 0.33361 (14) | 0.0270 (5) | |
C12 | 0.5444 (2) | 1.2363 (4) | 0.37161 (14) | 0.0285 (5) | |
H12 | 0.639 | 1.2399 | 0.3633 | 0.034* | |
C13 | 0.4873 (3) | 1.4074 (4) | 0.42123 (15) | 0.0332 (6) | |
H13 | 0.5423 | 1.5279 | 0.4461 | 0.04* | |
C14 | 0.3498 (3) | 1.4022 (4) | 0.43452 (16) | 0.0371 (6) | |
H14 | 0.3097 | 1.5201 | 0.4676 | 0.044* | |
C15 | 0.2714 (3) | 1.2235 (4) | 0.39914 (15) | 0.0361 (6) | |
H15 | 0.1775 | 1.2176 | 0.4094 | 0.043* | |
C16 | 0.3276 (2) | 1.0533 (4) | 0.34903 (14) | 0.0319 (5) | |
H16 | 0.2722 | 0.9322 | 0.325 | 0.038* | |
C21 | 0.3309 (2) | 0.8059 (4) | 0.16769 (14) | 0.0255 (5) | |
C22 | 0.3059 (2) | 1.0201 (4) | 0.12891 (14) | 0.0316 (6) | |
H22 | 0.3746 | 1.1341 | 0.1333 | 0.038* | |
C23 | 0.1818 (2) | 1.0672 (4) | 0.08406 (16) | 0.0366 (6) | |
H23 | 0.166 | 1.2121 | 0.0565 | 0.044* | |
C24 | 0.0801 (3) | 0.9029 (4) | 0.07927 (16) | 0.0369 (6) | |
H24 | −0.0052 | 0.9352 | 0.0484 | 0.044* | |
C25 | 0.1030 (2) | 0.6930 (4) | 0.11928 (16) | 0.0365 (6) | |
H25 | 0.0326 | 0.582 | 0.1171 | 0.044* | |
C26 | 0.2289 (2) | 0.6427 (4) | 0.16295 (15) | 0.0320 (6) | |
H26 | 0.2448 | 0.4966 | 0.1894 | 0.038* | |
C41 | 0.6601 (2) | 0.1923 (4) | 0.09970 (15) | 0.0307 (5) | |
C42 | 0.6118 (2) | 0.0785 (4) | 0.03937 (16) | 0.0373 (6) | |
H42 | 0.5733 | −0.0123 | −0.0087 | 0.045* | |
C71 | 0.9288 (2) | 0.7345 (4) | 0.37642 (16) | 0.0340 (6) | |
C72 | 0.9893 (3) | 0.8406 (5) | 0.43310 (19) | 0.0483 (7) | |
H72 | 1.0382 | 0.9261 | 0.4789 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0302 (11) | 0.0244 (10) | 0.0268 (10) | −0.0024 (8) | 0.0019 (8) | 0.0030 (8) |
N2 | 0.0294 (10) | 0.0221 (10) | 0.0254 (10) | 0.0004 (8) | 0.0009 (8) | 0.0024 (8) |
C1 | 0.0283 (13) | 0.0226 (12) | 0.0253 (12) | −0.0011 (9) | 0.0019 (10) | 0.0022 (10) |
C2 | 0.0279 (13) | 0.0210 (11) | 0.0250 (12) | −0.0011 (9) | 0.0036 (10) | 0.0029 (10) |
C3 | 0.0277 (12) | 0.0224 (11) | 0.0232 (11) | 0.0003 (9) | 0.0028 (10) | 0.0042 (9) |
C4 | 0.0315 (13) | 0.0267 (12) | 0.0260 (12) | −0.0003 (10) | 0.0044 (10) | 0.0035 (9) |
C5 | 0.0348 (14) | 0.0297 (13) | 0.0382 (14) | 0.0056 (11) | 0.0050 (11) | 0.0005 (11) |
C6 | 0.0294 (13) | 0.0393 (14) | 0.0392 (14) | 0.0049 (11) | −0.0003 (11) | 0.0028 (11) |
C7 | 0.0301 (13) | 0.0301 (13) | 0.0286 (12) | −0.0022 (10) | 0.0009 (10) | 0.0030 (10) |
C8 | 0.0287 (12) | 0.0251 (12) | 0.0252 (12) | −0.0017 (10) | 0.0017 (10) | 0.0041 (9) |
C11 | 0.0328 (13) | 0.0272 (12) | 0.0205 (11) | 0.0014 (10) | −0.0003 (9) | 0.0013 (9) |
C12 | 0.0376 (13) | 0.0259 (12) | 0.0218 (11) | −0.0016 (10) | 0.0004 (10) | 0.0032 (10) |
C13 | 0.0465 (15) | 0.0243 (12) | 0.0279 (13) | −0.0012 (11) | −0.0033 (11) | −0.0008 (10) |
C14 | 0.0475 (15) | 0.0309 (13) | 0.0324 (13) | 0.0075 (11) | −0.0003 (12) | −0.0035 (11) |
C15 | 0.0346 (13) | 0.0420 (14) | 0.0319 (13) | 0.0067 (11) | 0.0029 (11) | −0.0026 (12) |
C16 | 0.0334 (13) | 0.0358 (13) | 0.0262 (12) | 0.0003 (11) | −0.0008 (10) | −0.0032 (11) |
C21 | 0.0281 (12) | 0.0260 (13) | 0.0225 (12) | 0.0006 (10) | 0.0023 (9) | −0.0024 (10) |
C22 | 0.0343 (14) | 0.0280 (12) | 0.0320 (13) | 0.0005 (10) | −0.0010 (11) | −0.0007 (10) |
C23 | 0.0400 (15) | 0.0305 (13) | 0.0378 (14) | 0.0068 (11) | −0.0076 (11) | −0.0028 (11) |
C24 | 0.0353 (14) | 0.0402 (15) | 0.0340 (14) | 0.0061 (12) | −0.0052 (11) | −0.0094 (11) |
C25 | 0.0324 (14) | 0.0413 (15) | 0.0355 (14) | −0.0063 (11) | 0.0010 (11) | −0.0058 (12) |
C26 | 0.0369 (14) | 0.0276 (12) | 0.0312 (13) | −0.0034 (10) | 0.0009 (11) | −0.0014 (10) |
C41 | 0.0357 (13) | 0.0263 (12) | 0.0309 (13) | 0.0054 (10) | 0.0087 (11) | 0.0017 (11) |
C42 | 0.0461 (16) | 0.0344 (14) | 0.0315 (14) | −0.0014 (12) | 0.0037 (12) | −0.0040 (12) |
C71 | 0.0296 (13) | 0.0366 (14) | 0.0352 (14) | −0.0013 (11) | −0.0011 (11) | 0.0055 (11) |
C72 | 0.0458 (17) | 0.0528 (17) | 0.0452 (16) | −0.0149 (14) | −0.0054 (13) | −0.0008 (14) |
Geometric parameters (Å, º) top
N1—C1 | 1.323 (3) | C13—H13 | 0.9500 |
N1—C8 | 1.365 (3) | C14—C15 | 1.384 (3) |
N2—C2 | 1.324 (3) | C14—H14 | 0.9500 |
N2—C3 | 1.367 (3) | C15—C16 | 1.383 (3) |
C1—C2 | 1.441 (3) | C15—H15 | 0.9500 |
C1—C11 | 1.488 (3) | C16—H16 | 0.9500 |
C2—C21 | 1.494 (3) | C21—C26 | 1.386 (3) |
C3—C8 | 1.406 (3) | C21—C22 | 1.395 (3) |
C3—C4 | 1.431 (3) | C22—C23 | 1.383 (3) |
C4—C5 | 1.379 (3) | C22—H22 | 0.9500 |
C4—C41 | 1.436 (3) | C23—C24 | 1.388 (3) |
C5—C6 | 1.396 (3) | C23—H23 | 0.9500 |
C5—H5 | 0.9500 | C24—C25 | 1.377 (4) |
C6—C7 | 1.382 (3) | C24—H24 | 0.9500 |
C6—H6 | 0.9500 | C25—C26 | 1.394 (3) |
C7—C8 | 1.428 (3) | C25—H25 | 0.9500 |
C7—C71 | 1.437 (3) | C26—H26 | 0.9500 |
C11—C16 | 1.391 (3) | C41—C42 | 1.191 (3) |
C11—C12 | 1.399 (3) | C42—H42 | 0.9500 |
C12—C13 | 1.387 (3) | C71—C72 | 1.177 (3) |
C12—H12 | 0.9500 | C72—H72 | 0.9500 |
C13—C14 | 1.385 (3) | | |
| | | |
C1—N1—C8 | 117.99 (18) | C14—C13—H13 | 120.1 |
C2—N2—C3 | 117.56 (18) | C12—C13—H13 | 120.1 |
N1—C1—C2 | 120.63 (18) | C15—C14—C13 | 119.4 (2) |
N1—C1—C11 | 115.38 (18) | C15—C14—H14 | 120.3 |
C2—C1—C11 | 123.96 (18) | C13—C14—H14 | 120.3 |
N2—C2—C1 | 121.66 (18) | C16—C15—C14 | 121.0 (2) |
N2—C2—C21 | 115.08 (18) | C16—C15—H15 | 119.5 |
C1—C2—C21 | 123.24 (18) | C14—C15—H15 | 119.5 |
N2—C3—C8 | 120.76 (19) | C15—C16—C11 | 120.3 (2) |
N2—C3—C4 | 119.35 (19) | C15—C16—H16 | 119.8 |
C8—C3—C4 | 119.89 (19) | C11—C16—H16 | 119.8 |
C5—C4—C3 | 118.5 (2) | C26—C21—C22 | 119.4 (2) |
C5—C4—C41 | 120.8 (2) | C26—C21—C2 | 119.89 (19) |
C3—C4—C41 | 120.7 (2) | C22—C21—C2 | 120.6 (2) |
C4—C5—C6 | 121.4 (2) | C23—C22—C21 | 120.3 (2) |
C4—C5—H5 | 119.3 | C23—C22—H22 | 119.8 |
C6—C5—H5 | 119.3 | C21—C22—H22 | 119.8 |
C7—C6—C5 | 121.5 (2) | C22—C23—C24 | 120.0 (2) |
C7—C6—H6 | 119.2 | C22—C23—H23 | 120.0 |
C5—C6—H6 | 119.2 | C24—C23—H23 | 120.0 |
C6—C7—C8 | 118.4 (2) | C25—C24—C23 | 120.0 (2) |
C6—C7—C71 | 121.1 (2) | C25—C24—H24 | 120.0 |
C8—C7—C71 | 120.5 (2) | C23—C24—H24 | 120.0 |
N1—C8—C3 | 121.17 (19) | C24—C25—C26 | 120.3 (2) |
N1—C8—C7 | 118.53 (19) | C24—C25—H25 | 119.8 |
C3—C8—C7 | 120.16 (19) | C26—C25—H25 | 119.8 |
C16—C11—C12 | 118.4 (2) | C21—C26—C25 | 119.9 (2) |
C16—C11—C1 | 123.0 (2) | C21—C26—H26 | 120.0 |
C12—C11—C1 | 118.46 (19) | C25—C26—H26 | 120.0 |
C13—C12—C11 | 121.0 (2) | C42—C41—C4 | 177.4 (2) |
C13—C12—H12 | 119.5 | C41—C42—H42 | 180.0 |
C11—C12—H12 | 119.5 | C72—C71—C7 | 177.4 (3) |
C14—C13—C12 | 119.9 (2) | C71—C72—H72 | 180.0 |
| | | |
C8—N1—C1—C2 | −3.3 (3) | N1—C1—C11—C16 | −144.9 (2) |
C8—N1—C1—C11 | 175.23 (17) | C2—C1—C11—C16 | 33.5 (3) |
C3—N2—C2—C1 | −1.9 (3) | N1—C1—C11—C12 | 30.8 (3) |
C3—N2—C2—C21 | 176.27 (18) | C2—C1—C11—C12 | −150.72 (19) |
N1—C1—C2—N2 | 4.9 (3) | C16—C11—C12—C13 | −1.9 (3) |
C11—C1—C2—N2 | −173.42 (19) | C1—C11—C12—C13 | −177.89 (19) |
N1—C1—C2—C21 | −173.1 (2) | C11—C12—C13—C14 | 0.7 (3) |
C11—C1—C2—C21 | 8.5 (3) | C12—C13—C14—C15 | 1.0 (3) |
C2—N2—C3—C8 | −2.3 (3) | C13—C14—C15—C16 | −1.5 (3) |
C2—N2—C3—C4 | 177.20 (18) | C14—C15—C16—C11 | 0.3 (3) |
N2—C3—C4—C5 | −177.6 (2) | C12—C11—C16—C15 | 1.4 (3) |
C8—C3—C4—C5 | 2.0 (3) | C1—C11—C16—C15 | 177.2 (2) |
N2—C3—C4—C41 | 3.4 (3) | N2—C2—C21—C26 | 57.6 (3) |
C8—C3—C4—C41 | −177.1 (2) | C1—C2—C21—C26 | −124.2 (2) |
C3—C4—C5—C6 | −2.4 (3) | N2—C2—C21—C22 | −119.5 (2) |
C41—C4—C5—C6 | 176.7 (2) | C1—C2—C21—C22 | 58.7 (3) |
C4—C5—C6—C7 | 0.6 (3) | C26—C21—C22—C23 | −1.7 (3) |
C5—C6—C7—C8 | 1.6 (3) | C2—C21—C22—C23 | 175.4 (2) |
C5—C6—C7—C71 | −179.5 (2) | C21—C22—C23—C24 | 1.5 (3) |
C1—N1—C8—C3 | −1.0 (3) | C22—C23—C24—C25 | 0.1 (4) |
C1—N1—C8—C7 | −176.81 (19) | C23—C24—C25—C26 | −1.4 (4) |
N2—C3—C8—N1 | 4.0 (3) | C22—C21—C26—C25 | 0.3 (3) |
C4—C3—C8—N1 | −175.58 (19) | C2—C21—C26—C25 | −176.8 (2) |
N2—C3—C8—C7 | 179.74 (19) | C24—C25—C26—C21 | 1.2 (3) |
C4—C3—C8—C7 | 0.2 (3) | C5—C4—C41—C42 | −16 (5) |
C6—C7—C8—N1 | 173.93 (19) | C3—C4—C41—C42 | 163 (5) |
C71—C7—C8—N1 | −5.0 (3) | C6—C7—C71—C72 | −18 (6) |
C6—C7—C8—C3 | −2.0 (3) | C8—C7—C71—C72 | 161 (6) |
C71—C7—C8—C3 | 179.1 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C42—H42···N2i | 0.95 | 2.64 | 3.374 (3) | 135 |
Symmetry code: (i) −x+1, y−1/2, −z. |
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