5,8-Diethynyl-2,3-di­phenyl­quinoxaline

The title compound, C₂₄H₁₄N₂, 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[triple bond]C groups.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](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

---

Computing details

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).

(I)

Crystal data

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) Å^3	Plate, colourless
Z = 2	0.23 × 0.09 × 0.04 mm

Data collection

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

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0417P)^2 + 0.0338P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max < 0.001
wR(F^2) = 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+0.001xFc^2λ^3/sin(2θ)]^-1/4
236 parameters	Extinction coefficient: 0.041 (5)
244 restraints	Absolute structure: see text

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C42—H42···N2^i	0.95	2.64	3.374 (3)	135

Symmetry code: (i) −x+1, y−1/2, −z.