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The title compound, C
17H
9N
3O, is built up from two planar groups (quinoline and phthalonitrile), with a dihedral angle of 53.96 (5)° between them. The crystal structure is stabilized by weak C—H
N hydrogen-bond and C—N
π interactions.
Supporting information
CCDC reference: 624014
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.122
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT481_ALERT_4_B Long D...A H-Bond Reported C16 .. CG .. 4.74 Ang.
Alert level C
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C11 - C16 ... 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C12 - C17 ... 1.43 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 40
C10 -C11 -C16 -N2 7.00 0.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 41
C12 -C11 -C16 -N2 11.00 0.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 42
C13 -C12 -C17 -N3 66.00 9.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 43
C11 -C12 -C17 -N3 -113.00 9.00 1.555 1.555 1.555 1.555
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
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXL97.
3-(4-Quinolinoxy)phthalonitrile
top
Crystal data top
C17H9N3O | F(000) = 560 |
Mr = 271.27 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/c | Melting point = 478–479 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71069 Å |
a = 8.500 (5) Å | Cell parameters from 3144 reflections |
b = 12.679 (6) Å | θ = 12–18° |
c = 12.428 (6) Å | µ = 0.09 mm−1 |
β = 99.96 (2)° | T = 293 K |
V = 1319.2 (11) Å3 | Needle, colourless |
Z = 4 | 0.50 × 0.10 × 0.05 mm |
Data collection top
Rigaku Weissenberg IP diffractometer | 1707 reflections with I > 2σ(I) |
Radiation source: rotor target | Rint = 0.046 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
scintillation counter scans | h = −11→11 |
12608 measured reflections | k = −16→16 |
3003 independent reflections | l = −16→14 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0581P)2] where P = (Fo2 + 2Fc2)/3 |
3003 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.5305 (2) | 0.40542 (11) | −0.15685 (11) | 0.0509 (4) | |
N2 | 0.9594 (2) | 0.06471 (13) | 0.24254 (15) | 0.0790 (6) | |
N3 | 1.1304 (3) | 0.17430 (17) | 0.54161 (16) | 0.0884 (6) | |
O1 | 0.69492 (15) | 0.25453 (8) | 0.13915 (9) | 0.0533 (3) | |
C1 | 0.6390 (2) | 0.44883 (13) | −0.08258 (14) | 0.0505 (5) | |
H1 | 0.6787 | 0.5141 | −0.0991 | 0.062 (5)* | |
C2 | 0.7007 (2) | 0.40533 (13) | 0.01981 (14) | 0.0471 (4) | |
H2 | 0.7793 | 0.4399 | 0.0686 | 0.060 (6)* | |
C3 | 0.6412 (2) | 0.31072 (12) | 0.04489 (12) | 0.0403 (4) | |
C4 | 0.4589 (2) | 0.15894 (13) | −0.01144 (13) | 0.0450 (4) | |
H4 | 0.4915 | 0.1248 | 0.0549 | 0.056 (5)* | |
C5 | 0.3496 (2) | 0.11300 (14) | −0.08990 (14) | 0.0508 (5) | |
H5 | 0.3085 | 0.0471 | −0.0772 | 0.063 (6)* | |
C6 | 0.2980 (2) | 0.16353 (14) | −0.18950 (14) | 0.0532 (5) | |
H6 | 0.2225 | 0.1312 | −0.2423 | 0.061 (5)* | |
C7 | 0.3570 (2) | 0.25958 (14) | −0.20984 (14) | 0.0515 (5) | |
H7 | 0.3210 | 0.2927 | −0.2763 | 0.065 (6)* | |
C8 | 0.4720 (2) | 0.30954 (12) | −0.13161 (12) | 0.0417 (4) | |
C9 | 0.52358 (19) | 0.25881 (12) | −0.03037 (12) | 0.0384 (4) | |
C10 | 0.7568 (2) | 0.30309 (12) | 0.23550 (12) | 0.0402 (4) | |
C11 | 0.87009 (19) | 0.24487 (11) | 0.30436 (13) | 0.0386 (4) | |
C12 | 0.9314 (2) | 0.28465 (13) | 0.40830 (12) | 0.0429 (4) | |
C13 | 0.8812 (2) | 0.38159 (13) | 0.44046 (14) | 0.0503 (5) | |
H13 | 0.9224 | 0.4086 | 0.5092 | 0.059 (5)* | |
C14 | 0.7053 (2) | 0.39951 (13) | 0.26821 (13) | 0.0462 (4) | |
H14 | 0.6281 | 0.4380 | 0.2222 | 0.062 (6)* | |
C15 | 0.7699 (2) | 0.43751 (13) | 0.36976 (14) | 0.0507 (5) | |
H15 | 0.7372 | 0.5031 | 0.3912 | 0.075 (6)* | |
C16 | 0.9206 (2) | 0.14458 (14) | 0.26984 (14) | 0.0487 (4) | |
C17 | 1.0436 (2) | 0.22328 (15) | 0.48184 (15) | 0.0555 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0606 (11) | 0.0463 (7) | 0.0453 (8) | 0.0058 (7) | 0.0076 (8) | 0.0102 (7) |
N2 | 0.0864 (15) | 0.0639 (10) | 0.0868 (13) | 0.0198 (10) | 0.0155 (11) | −0.0088 (10) |
N3 | 0.0800 (15) | 0.1026 (15) | 0.0689 (12) | 0.0062 (12) | −0.0254 (11) | 0.0222 (11) |
O1 | 0.0670 (9) | 0.0447 (6) | 0.0393 (6) | 0.0018 (6) | −0.0161 (6) | 0.0031 (5) |
C1 | 0.0591 (13) | 0.0435 (9) | 0.0502 (10) | 0.0007 (8) | 0.0132 (10) | 0.0056 (8) |
C2 | 0.0462 (11) | 0.0458 (9) | 0.0478 (10) | −0.0002 (8) | 0.0041 (9) | −0.0025 (8) |
C3 | 0.0426 (10) | 0.0413 (8) | 0.0350 (8) | 0.0080 (7) | 0.0007 (7) | 0.0038 (7) |
C4 | 0.0479 (11) | 0.0475 (9) | 0.0383 (9) | 0.0017 (8) | 0.0042 (8) | 0.0056 (7) |
C5 | 0.0509 (12) | 0.0531 (10) | 0.0475 (10) | −0.0062 (8) | 0.0059 (9) | −0.0006 (8) |
C6 | 0.0471 (12) | 0.0653 (11) | 0.0439 (10) | −0.0056 (9) | −0.0013 (8) | −0.0070 (9) |
C7 | 0.0493 (11) | 0.0648 (11) | 0.0368 (9) | 0.0076 (9) | −0.0027 (8) | 0.0065 (8) |
C8 | 0.0409 (10) | 0.0461 (9) | 0.0371 (8) | 0.0081 (7) | 0.0035 (7) | 0.0056 (7) |
C9 | 0.0373 (9) | 0.0421 (8) | 0.0352 (8) | 0.0065 (7) | 0.0046 (7) | 0.0019 (7) |
C10 | 0.0400 (10) | 0.0422 (8) | 0.0358 (8) | −0.0018 (7) | −0.0006 (7) | 0.0019 (7) |
C11 | 0.0366 (9) | 0.0413 (8) | 0.0368 (8) | 0.0007 (7) | 0.0037 (7) | 0.0035 (7) |
C12 | 0.0390 (10) | 0.0514 (9) | 0.0362 (8) | −0.0063 (8) | 0.0007 (7) | 0.0055 (7) |
C13 | 0.0629 (13) | 0.0511 (10) | 0.0360 (9) | −0.0091 (9) | 0.0062 (9) | −0.0041 (8) |
C14 | 0.0480 (11) | 0.0438 (9) | 0.0461 (10) | 0.0070 (8) | 0.0062 (9) | 0.0081 (8) |
C15 | 0.0650 (14) | 0.0434 (9) | 0.0467 (10) | 0.0007 (9) | 0.0178 (10) | −0.0017 (8) |
C16 | 0.0499 (11) | 0.0478 (9) | 0.0460 (9) | 0.0078 (8) | 0.0020 (8) | 0.0022 (8) |
C17 | 0.0521 (12) | 0.0671 (12) | 0.0418 (10) | −0.0057 (10) | −0.0080 (9) | 0.0075 (9) |
Geometric parameters (Å, º) top
N1—C1 | 1.308 (2) | C6—C7 | 1.358 (2) |
N1—C8 | 1.370 (2) | C6—H6 | 0.9300 |
N2—C16 | 1.135 (2) | C7—C8 | 1.405 (2) |
N3—C17 | 1.137 (2) | C7—H7 | 0.9300 |
O1—C10 | 1.3683 (19) | C8—C9 | 1.414 (2) |
O1—C3 | 1.3797 (18) | C10—C14 | 1.383 (2) |
C1—C2 | 1.403 (2) | C10—C11 | 1.385 (2) |
C1—H1 | 0.9300 | C11—C12 | 1.401 (2) |
C2—C3 | 1.359 (2) | C11—C16 | 1.432 (2) |
C2—H2 | 0.9300 | C12—C13 | 1.383 (2) |
C3—C9 | 1.409 (2) | C12—C17 | 1.431 (3) |
C4—C5 | 1.357 (2) | C13—C15 | 1.372 (3) |
C4—C9 | 1.416 (2) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—C15 | 1.374 (2) |
C5—C6 | 1.396 (3) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
| | | |
C1—N1—C8 | 116.82 (15) | C7—C8—C9 | 118.84 (15) |
C10—O1—C3 | 122.10 (13) | C3—C9—C8 | 116.98 (14) |
N1—C1—C2 | 125.59 (16) | C3—C9—C4 | 123.97 (14) |
N1—C1—H1 | 117.2 | C8—C9—C4 | 119.03 (15) |
C2—C1—H1 | 117.2 | O1—C10—C14 | 124.15 (15) |
C3—C2—C1 | 117.36 (17) | O1—C10—C11 | 114.96 (14) |
C3—C2—H2 | 121.3 | C14—C10—C11 | 120.73 (15) |
C1—C2—H2 | 121.3 | C10—C11—C12 | 119.07 (14) |
C2—C3—O1 | 124.66 (16) | C10—C11—C16 | 120.04 (15) |
C2—C3—C9 | 120.65 (15) | C12—C11—C16 | 120.88 (15) |
O1—C3—C9 | 114.54 (14) | C13—C12—C11 | 120.18 (16) |
C5—C4—C9 | 120.12 (16) | C13—C12—C17 | 120.22 (16) |
C5—C4—H4 | 119.9 | C11—C12—C17 | 119.59 (15) |
C9—C4—H4 | 119.9 | C15—C13—C12 | 119.16 (16) |
C4—C5—C6 | 120.77 (16) | C15—C13—H13 | 120.4 |
C4—C5—H5 | 119.6 | C12—C13—H13 | 120.4 |
C6—C5—H5 | 119.6 | C15—C14—C10 | 118.90 (17) |
C7—C6—C5 | 120.48 (18) | C15—C14—H14 | 120.6 |
C7—C6—H6 | 119.8 | C10—C14—H14 | 120.6 |
C5—C6—H6 | 119.8 | C13—C15—C14 | 121.94 (16) |
C6—C7—C8 | 120.74 (16) | C13—C15—H15 | 119.0 |
C6—C7—H7 | 119.6 | C14—C15—H15 | 119.0 |
C8—C7—H7 | 119.6 | N2—C16—C11 | 179.4 (2) |
N1—C8—C7 | 118.57 (14) | N3—C17—C12 | 178.6 (2) |
N1—C8—C9 | 122.59 (16) | | |
| | | |
C8—N1—C1—C2 | 0.4 (3) | C5—C4—C9—C8 | 0.2 (2) |
N1—C1—C2—C3 | −1.0 (3) | C3—O1—C10—C14 | 34.1 (2) |
C1—C2—C3—O1 | 176.16 (15) | C3—O1—C10—C11 | −150.47 (15) |
C1—C2—C3—C9 | 0.8 (2) | O1—C10—C11—C12 | −175.21 (13) |
C10—O1—C3—C2 | 30.4 (2) | C14—C10—C11—C12 | 0.4 (2) |
C10—O1—C3—C9 | −153.94 (14) | O1—C10—C11—C16 | 3.5 (2) |
C9—C4—C5—C6 | −0.7 (3) | C14—C10—C11—C16 | 179.16 (15) |
C4—C5—C6—C7 | 0.3 (3) | C10—C11—C12—C13 | −1.2 (2) |
C5—C6—C7—C8 | 0.5 (3) | C16—C11—C12—C13 | −179.92 (16) |
C1—N1—C8—C7 | −179.05 (16) | C10—C11—C12—C17 | 177.45 (15) |
C1—N1—C8—C9 | 0.5 (2) | C16—C11—C12—C17 | −1.3 (2) |
C6—C7—C8—N1 | 178.63 (15) | C11—C12—C13—C15 | 0.6 (2) |
C6—C7—C8—C9 | −1.0 (2) | C17—C12—C13—C15 | −178.00 (16) |
C2—C3—C9—C8 | 0.1 (2) | O1—C10—C14—C15 | 176.10 (15) |
O1—C3—C9—C8 | −175.79 (13) | C11—C10—C14—C15 | 0.9 (2) |
C2—C3—C9—C4 | 178.22 (15) | C12—C13—C15—C14 | 0.7 (3) |
O1—C3—C9—C4 | 2.4 (2) | C10—C14—C15—C13 | −1.5 (3) |
N1—C8—C9—C3 | −0.7 (2) | C10—C11—C16—N2 | −70 (20) |
C7—C8—C9—C3 | 178.84 (14) | C12—C11—C16—N2 | 109 (20) |
N1—C8—C9—C4 | −178.99 (14) | C13—C12—C17—N3 | 66 (9) |
C7—C8—C9—C4 | 0.6 (2) | C11—C12—C17—N3 | −113 (9) |
C5—C4—C9—C3 | −177.88 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N1i | 0.93 | 2.46 | 3.330 (2) | 156 |
C1—H1···N3ii | 0.93 | 2.62 | 3.454 (3) | 149 |
C16—N2···Cgiii | 1.14 (1) | 3.63 (1) | 4.737 (3) | 166 (1) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2. |
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