Download citation
Download citation
link to html
In the title compound, C17H9N3O, the dihedral angle between the quinoline group and the dicyanobenzene ring is 66.54 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042893/is6165sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042893/is6165Isup2.hkl
Contains datablock I

CCDC reference: 298713

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.125
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 20 Ang. PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 6.80 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C13 - C17 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C15 - C16 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 4 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

4-(Quinolin-4-yloxy)phthalonitrile top
Crystal data top
C17H9N3ODx = 1.325 Mg m3
Mr = 271.27Melting point: 448.2-449 K K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 7.1044 (5) ÅCell parameters from 11450 reflections
b = 15.5318 (8) Åθ = 1.6–27.5°
c = 24.6393 (2) ŵ = 0.09 mm1
V = 2718.8 (2) Å3T = 293 K
Z = 8Block, colourless
F(000) = 11200.55 × 0.20 × 0.10 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3047 independent reflections
Radiation source: rotor target1821 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 09
Tmin = 0.908, Tmax = 0.989k = 020
15500 measured reflectionsl = 031
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.1058P]
where P = (Fo2 + 2Fc2)/3
3047 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.12 e Å3
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
xyzUiso*/Ueq
O10.16841 (17)0.43874 (8)0.43363 (4)0.0764 (4)
N10.1471 (2)0.31440 (10)0.55325 (6)0.0685 (4)
N20.1413 (3)0.17152 (11)0.26510 (7)0.0970 (6)
N30.1379 (2)0.37628 (11)0.16446 (6)0.0868 (5)
C10.0313 (2)0.34363 (10)0.56280 (6)0.0590 (4)
C20.1081 (3)0.33231 (14)0.61487 (7)0.0819 (6)
H20.03690.30340.64190.098*
C30.2812 (3)0.36192 (17)0.62689 (9)0.1022 (8)
H30.33010.35440.66250.123*
C40.3894 (3)0.40345 (17)0.58767 (9)0.1001 (7)
H40.51110.42420.59680.120*
C50.3227 (3)0.41475 (13)0.53634 (8)0.0770 (5)
H50.39850.44230.50970.092*
C60.1408 (2)0.38546 (10)0.52284 (6)0.0550 (4)
C70.0597 (2)0.39446 (9)0.47104 (6)0.0555 (4)
C80.1164 (2)0.36456 (11)0.46116 (6)0.0629 (4)
H80.17230.37000.42630.075*
C90.2128 (2)0.32555 (11)0.50396 (7)0.0674 (5)
H90.33650.30530.49680.081*
C100.1516 (2)0.42115 (10)0.37898 (6)0.0573 (4)
C110.1525 (2)0.49150 (11)0.34465 (6)0.0651 (5)
H110.15630.54820.35910.078*
C120.1480 (2)0.47901 (10)0.28949 (6)0.0641 (4)
H120.14810.52720.26580.077*
C130.1432 (2)0.39662 (10)0.26827 (6)0.0523 (4)
C140.1491 (2)0.33802 (10)0.35933 (6)0.0569 (4)
H140.15060.29020.38340.068*
C150.1445 (2)0.32601 (9)0.30356 (6)0.0514 (4)
C160.1437 (2)0.23993 (12)0.28210 (6)0.0657 (5)
C170.1402 (2)0.38431 (11)0.21025 (7)0.0623 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1022 (9)0.0830 (8)0.0441 (6)0.0301 (7)0.0063 (6)0.0032 (6)
N10.0749 (10)0.0706 (9)0.0602 (9)0.0024 (8)0.0116 (7)0.0026 (7)
N20.1400 (16)0.0660 (10)0.0850 (12)0.0099 (10)0.0194 (11)0.0115 (9)
N30.1006 (12)0.1108 (13)0.0490 (8)0.0053 (10)0.0088 (9)0.0006 (9)
C10.0688 (10)0.0615 (9)0.0467 (8)0.0106 (8)0.0058 (8)0.0004 (7)
C20.0880 (14)0.1058 (15)0.0520 (10)0.0224 (12)0.0033 (10)0.0124 (10)
C30.0941 (16)0.155 (2)0.0573 (11)0.0318 (15)0.0120 (12)0.0022 (13)
C40.0731 (13)0.151 (2)0.0766 (14)0.0041 (13)0.0195 (12)0.0208 (14)
C50.0678 (11)0.0959 (14)0.0675 (11)0.0072 (10)0.0007 (9)0.0115 (10)
C60.0613 (9)0.0560 (8)0.0476 (8)0.0041 (7)0.0018 (7)0.0081 (7)
C70.0725 (10)0.0521 (8)0.0421 (8)0.0036 (7)0.0078 (8)0.0027 (7)
C80.0714 (11)0.0705 (10)0.0467 (8)0.0026 (8)0.0044 (8)0.0069 (8)
C90.0661 (10)0.0722 (11)0.0640 (11)0.0054 (8)0.0052 (9)0.0111 (9)
C100.0646 (9)0.0673 (10)0.0400 (8)0.0058 (8)0.0041 (7)0.0010 (7)
C110.0840 (12)0.0556 (9)0.0557 (10)0.0015 (8)0.0046 (9)0.0020 (7)
C120.0802 (11)0.0577 (9)0.0544 (9)0.0002 (8)0.0022 (8)0.0093 (7)
C130.0506 (8)0.0621 (9)0.0442 (7)0.0015 (7)0.0039 (7)0.0048 (6)
C140.0671 (10)0.0564 (9)0.0471 (8)0.0007 (7)0.0038 (7)0.0064 (7)
C150.0524 (8)0.0552 (8)0.0465 (8)0.0037 (7)0.0066 (7)0.0008 (7)
C160.0787 (11)0.0638 (10)0.0545 (10)0.0077 (9)0.0121 (8)0.0012 (8)
C170.0648 (10)0.0741 (11)0.0478 (9)0.0018 (8)0.0072 (8)0.0063 (8)
Geometric parameters (Å, º) top
O1—C101.3790 (18)C6—C71.407 (2)
O1—C71.3852 (18)C7—C81.357 (2)
N1—C91.313 (2)C8—C91.396 (2)
N1—C11.367 (2)C8—H80.9500
N2—C161.142 (2)C9—H90.9500
N3—C171.135 (2)C10—C141.379 (2)
C1—C21.405 (2)C10—C111.382 (2)
C1—C61.413 (2)C11—C121.373 (2)
C2—C31.346 (3)C11—H110.9500
C2—H20.9500C12—C131.383 (2)
C3—C41.393 (3)C12—H120.9500
C3—H30.9500C13—C151.400 (2)
C4—C51.362 (3)C13—C171.443 (2)
C4—H40.9500C14—C151.3872 (19)
C5—C61.410 (2)C14—H140.9500
C5—H50.9500C15—C161.438 (2)
C10—O1—C7120.20 (12)C9—C8—H8121.1
C9—N1—C1116.44 (15)N1—C9—C8125.59 (16)
N1—C1—C2118.41 (17)N1—C9—H9117.2
N1—C1—C6122.91 (15)C8—C9—H9117.2
C2—C1—C6118.68 (17)O1—C10—C14121.96 (14)
C3—C2—C1120.86 (19)O1—C10—C11116.14 (14)
C3—C2—H2119.6C14—C10—C11121.70 (14)
C1—C2—H2119.6C12—C11—C10119.60 (15)
C2—C3—C4120.63 (19)C12—C11—H11120.2
C2—C3—H3119.7C10—C11—H11120.2
C4—C3—H3119.7C11—C12—C13120.36 (14)
C5—C4—C3120.8 (2)C11—C12—H12119.8
C5—C4—H4119.6C13—C12—H12119.8
C3—C4—H4119.6C12—C13—C15119.36 (14)
C4—C5—C6119.75 (19)C12—C13—C17119.85 (14)
C4—C5—H5120.1C15—C13—C17120.79 (14)
C6—C5—H5120.1C10—C14—C15118.30 (14)
C7—C6—C5123.85 (15)C10—C14—H14120.9
C7—C6—C1116.90 (15)C15—C14—H14120.9
C5—C6—C1119.24 (15)C14—C15—C13120.67 (13)
C8—C7—O1124.38 (14)C14—C15—C16119.31 (13)
C8—C7—C6120.41 (15)C13—C15—C16120.01 (13)
O1—C7—C6115.14 (14)N2—C16—C15179.38 (19)
C7—C8—C9117.75 (15)N3—C17—C13178.69 (19)
C7—C8—H8121.1
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds