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In the crystal structure of the title compound, C
20H
10N
4O
2, the molecule is arranged around a twofold axis passing through the mid-point of the C
C triple bond. The dicyanophenoxy group is planar. The molecule is stabilized by intermolecular C—H
N hydrogen bonding.
Supporting information
CCDC reference: 608321
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.091
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C2 - C9 .. 7.36 su
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C8 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C9 ... 1.43 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996),
ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
1,4-Bis(3,4-dicyanophenoxy)-2-butyne
top
Crystal data top
C20H10N4O2 | F(000) = 696 |
Mr = 338.33 | Dx = 1.347 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8495 reflections |
a = 22.023 (7) Å | θ = 2.3–27.9° |
b = 9.570 (2) Å | µ = 0.09 mm−1 |
c = 8.339 (2) Å | T = 293 K |
β = 108.30 (2)° | Prism, colourless |
V = 1668.6 (8) Å3 | 0.75 × 0.21 × 0.06 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 1641 independent reflections |
Radiation source: fine-focus sealed tube | 1042 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.0° |
φ scans | h = −27→27 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −11→11 |
Tmin = 0.960, Tmax = 0.994 | l = −10→10 |
7313 measured reflections | |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.044P)2] where P = (Fo2 + 2Fc2)/3 |
1641 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.10 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Special details top
Experimental. Spectroscopic analysis: IR (νmax, cm-1): 3106–3080 (Ar—CH2),
2953–2902 (CH2), 2232 (CN), 1602, 1548, 1493, 1458, 1432, 1370, 1288, 1261,
1240, 1206, 1179, 1151, 1104, 1008, 906, 892, 844. |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.36367 (6) | 0.88643 (12) | 0.11015 (17) | 0.0755 (4) | |
C1 | 0.39139 (7) | 0.51004 (16) | 0.10260 (19) | 0.0516 (4) | |
C2 | 0.33874 (7) | 0.46213 (17) | 0.14759 (19) | 0.0543 (4) | |
C10 | 0.47546 (8) | 0.94407 (17) | 0.1944 (2) | 0.0649 (5) | |
C8 | 0.43366 (8) | 0.40934 (18) | 0.0651 (2) | 0.0587 (4) | |
C5 | 0.36031 (8) | 0.74626 (17) | 0.1233 (2) | 0.0581 (4) | |
C6 | 0.40233 (7) | 0.65118 (17) | 0.09082 (19) | 0.0557 (4) | |
H6 | 0.4375 | 0.6819 | 0.0614 | 0.067* | |
N2 | 0.46681 (8) | 0.32894 (17) | 0.0354 (2) | 0.0792 (5) | |
C3 | 0.29783 (8) | 0.55925 (19) | 0.1828 (2) | 0.0627 (5) | |
H3 | 0.2630 | 0.5292 | 0.2139 | 0.075* | |
C4 | 0.30878 (8) | 0.69890 (19) | 0.1717 (2) | 0.0640 (5) | |
H4 | 0.2815 | 0.7633 | 0.1968 | 0.077* | |
C9 | 0.32776 (8) | 0.3154 (2) | 0.1580 (2) | 0.0632 (4) | |
N1 | 0.31870 (8) | 0.1987 (2) | 0.1682 (2) | 0.0878 (5) | |
C19 | 0.41464 (8) | 0.94539 (19) | 0.0588 (3) | 0.0725 (5) | |
H19A | 0.4039 | 1.0409 | 0.0220 | 0.087* | |
H19B | 0.4190 | 0.8928 | −0.0364 | 0.087* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0673 (8) | 0.0571 (8) | 0.1083 (10) | 0.0058 (6) | 0.0363 (7) | 0.0022 (7) |
C1 | 0.0485 (8) | 0.0599 (10) | 0.0489 (8) | 0.0032 (7) | 0.0187 (7) | −0.0019 (7) |
C2 | 0.0519 (8) | 0.0595 (10) | 0.0540 (9) | 0.0012 (8) | 0.0203 (8) | 0.0026 (8) |
C10 | 0.0710 (12) | 0.0506 (9) | 0.0809 (14) | 0.0010 (7) | 0.0350 (10) | −0.0001 (8) |
C8 | 0.0598 (9) | 0.0616 (10) | 0.0616 (10) | −0.0012 (8) | 0.0289 (8) | −0.0037 (8) |
C5 | 0.0537 (9) | 0.0567 (10) | 0.0636 (10) | 0.0044 (8) | 0.0180 (8) | 0.0008 (8) |
C6 | 0.0515 (9) | 0.0615 (10) | 0.0598 (10) | −0.0005 (8) | 0.0254 (8) | −0.0010 (7) |
N2 | 0.0823 (10) | 0.0751 (11) | 0.0951 (12) | 0.0094 (9) | 0.0490 (9) | −0.0070 (9) |
C3 | 0.0522 (9) | 0.0716 (11) | 0.0713 (11) | 0.0050 (8) | 0.0297 (9) | 0.0055 (9) |
C4 | 0.0529 (9) | 0.0682 (11) | 0.0767 (11) | 0.0133 (8) | 0.0285 (9) | 0.0014 (9) |
C9 | 0.0550 (10) | 0.0702 (13) | 0.0701 (11) | 0.0027 (9) | 0.0281 (9) | 0.0049 (9) |
N1 | 0.0859 (11) | 0.0682 (11) | 0.1217 (15) | −0.0017 (9) | 0.0506 (11) | 0.0068 (10) |
C19 | 0.0736 (12) | 0.0590 (10) | 0.0860 (13) | −0.0002 (9) | 0.0264 (11) | 0.0093 (9) |
Geometric parameters (Å, º) top
O1—C5 | 1.350 (2) | C5—C6 | 1.384 (2) |
O1—C19 | 1.4366 (19) | C5—C4 | 1.394 (2) |
C1—C6 | 1.381 (2) | C6—H6 | 0.9300 |
C1—C2 | 1.403 (2) | C3—C4 | 1.366 (3) |
C1—C8 | 1.441 (2) | C3—H3 | 0.9300 |
C2—C3 | 1.389 (2) | C4—H4 | 0.9300 |
C2—C9 | 1.432 (3) | C9—N1 | 1.142 (2) |
C10—C10i | 1.183 (4) | C19—H19A | 0.9700 |
C10—C19 | 1.456 (2) | C19—H19B | 0.9700 |
C8—N2 | 1.140 (2) | | |
| | | |
C5—O1—C19 | 118.84 (13) | C5—C6—H6 | 120.4 |
C6—C1—C2 | 121.07 (13) | C4—C3—C2 | 120.02 (14) |
C6—C1—C8 | 119.97 (13) | C4—C3—H3 | 120.0 |
C2—C1—C8 | 118.95 (14) | C2—C3—H3 | 120.0 |
C3—C2—C1 | 118.90 (15) | C3—C4—C5 | 120.97 (15) |
C3—C2—C9 | 120.69 (13) | C3—C4—H4 | 119.5 |
C1—C2—C9 | 120.41 (14) | C5—C4—H4 | 119.5 |
C10i—C10—C19 | 179.2 (2) | N1—C9—C2 | 179.01 (18) |
N2—C8—C1 | 179.53 (17) | O1—C19—C10 | 112.29 (15) |
O1—C5—C6 | 125.48 (14) | O1—C19—H19A | 109.1 |
O1—C5—C4 | 114.64 (14) | C10—C19—H19A | 109.1 |
C6—C5—C4 | 119.87 (16) | O1—C19—H19B | 109.1 |
C1—C6—C5 | 119.13 (13) | C10—C19—H19B | 109.1 |
C1—C6—H6 | 120.4 | H19A—C19—H19B | 107.9 |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···N2ii | 0.93 | 2.48 | 3.369 (2) | 159 |
Symmetry code: (ii) −x+1, −y+1, −z. |
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