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In the title compound, C17H12N2O, the phthalo­nitrile group is coplanar with the three-atom bridge linking the phthalo­nitrile group with the indanyl­oxy group. The five-membered ring of the indanyl­oxy moiety adopts an envelope conformation. The crystal structure of the title compound is stabilized by two C—H...π interactions and van der Waals interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009699/hg6038sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009699/hg6038Isup2.hkl
Contains datablock I

CCDC reference: 239296

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.067
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 31 Perc.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.741 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C7 - C8 ... 1.45 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17A .. CG3 .. 2.99 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C17 .. CG3 .. 3.92 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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: 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-(1-Indanyloxy)phthalonitrile top
Crystal data top
C17H12N2OF(000) = 544
Mr = 260.29Dx = 1.289 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2365 reflections
a = 8.0560 (16) Åθ = 1.7–22.9°
b = 23.950 (3) ŵ = 0.08 mm1
c = 7.8057 (16) ÅT = 293 K
β = 117.069 (14)°Plate, colourless
V = 1341.1 (4) Å30.50 × 0.25 × 0.02 mm
Z = 4
Data collection top
STOE IPDS-II
diffractometer
2498 independent reflections
Radiation source: sealed X-ray tube767 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.086
Detector resolution: 6.67 pixels mm-1θmax = 25.5°, θmin = 1.7°
ω scansh = 99
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2826
Tmin = 0.979, Tmax = 0.998l = 99
9063 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0101P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.74(Δ/σ)max < 0.001
2498 reflectionsΔρmax = 0.12 e Å3
170 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0034 (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
xyzUiso*/Ueq
O10.1628 (3)0.40707 (8)0.4057 (3)0.0681 (6)
N10.3542 (4)0.13418 (10)0.5837 (4)0.1040 (10)
N20.7112 (4)0.24887 (12)0.9371 (4)0.0879 (9)
C10.3205 (4)0.18084 (13)0.5546 (4)0.0657 (6)
C20.2815 (4)0.23916 (13)0.5210 (4)0.0657 (6)
C30.1200 (4)0.25757 (12)0.3659 (4)0.0651 (9)
H30.03530.23180.28290.078*
C40.0842 (4)0.31382 (12)0.3339 (4)0.0636 (8)
H40.02530.32580.23030.076*
C50.2095 (4)0.35265 (12)0.4545 (4)0.0598 (8)
C60.3713 (4)0.33539 (12)0.6112 (4)0.0614 (8)
H60.45500.36140.69430.074*
C70.4064 (4)0.27865 (11)0.6421 (4)0.0628 (6)
C80.5773 (4)0.26110 (12)0.8064 (4)0.0628 (6)
C90.2969 (4)0.44940 (11)0.5174 (4)0.0626 (8)
H90.42250.43820.54100.075*
C100.2443 (4)0.50360 (12)0.4093 (4)0.0582 (8)
C110.2046 (4)0.51241 (12)0.2207 (4)0.0727 (9)
H110.20490.48300.14300.087*
C120.1637 (4)0.56676 (14)0.1489 (5)0.0817 (10)
H120.13180.57380.02040.098*
C130.1705 (4)0.61032 (13)0.2693 (6)0.0833 (11)
H130.14560.64650.22120.100*
C140.2136 (4)0.60071 (13)0.4582 (5)0.0770 (10)
H140.21910.63000.53870.092*
C150.2485 (4)0.54659 (14)0.5263 (4)0.0652 (9)
C160.2994 (5)0.52598 (12)0.7260 (4)0.0854 (10)
H16A0.21040.53890.76880.102*
H16B0.42290.53870.81630.102*
C170.2939 (4)0.46255 (12)0.7077 (4)0.0798 (10)
H17A0.18160.44790.70730.096*
H17B0.40110.44600.81440.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0636 (14)0.0512 (13)0.0704 (14)0.0076 (12)0.0137 (11)0.0003 (12)
N10.133 (3)0.0666 (18)0.101 (2)0.013 (2)0.043 (2)0.0006 (18)
N20.082 (2)0.085 (2)0.0776 (19)0.0043 (17)0.0201 (16)0.0106 (16)
C10.0784 (18)0.0566 (13)0.0589 (14)0.0011 (17)0.0285 (13)0.0023 (15)
C20.0784 (18)0.0566 (13)0.0589 (14)0.0011 (17)0.0285 (13)0.0023 (15)
C30.070 (2)0.060 (2)0.065 (2)0.015 (2)0.0293 (19)0.0095 (18)
C40.060 (2)0.062 (2)0.0578 (19)0.0026 (19)0.0177 (16)0.0030 (18)
C50.064 (2)0.049 (2)0.068 (2)0.002 (2)0.0316 (19)0.0010 (19)
C60.061 (2)0.056 (2)0.062 (2)0.0059 (18)0.0234 (18)0.0036 (17)
C70.0722 (18)0.0600 (15)0.0599 (16)0.0037 (15)0.0333 (13)0.0063 (14)
C80.0722 (18)0.0600 (15)0.0599 (16)0.0037 (15)0.0333 (13)0.0063 (14)
C90.064 (2)0.053 (2)0.064 (2)0.0092 (19)0.0232 (17)0.0022 (18)
C100.058 (2)0.0512 (19)0.064 (2)0.0057 (18)0.0258 (17)0.0034 (19)
C110.080 (2)0.060 (2)0.072 (2)0.002 (2)0.0294 (19)0.0057 (19)
C120.084 (3)0.079 (2)0.069 (2)0.002 (2)0.023 (2)0.009 (2)
C130.074 (3)0.062 (2)0.111 (3)0.005 (2)0.039 (2)0.014 (2)
C140.078 (3)0.062 (2)0.095 (3)0.003 (2)0.044 (2)0.009 (2)
C150.062 (2)0.059 (2)0.072 (2)0.0034 (19)0.0284 (19)0.004 (2)
C160.099 (3)0.082 (2)0.078 (2)0.003 (2)0.043 (2)0.010 (2)
C170.090 (3)0.082 (2)0.059 (2)0.012 (2)0.0269 (19)0.0019 (19)
Geometric parameters (Å, º) top
O1—C51.362 (3)C9—H90.9800
O1—C91.448 (3)C10—C151.367 (3)
N1—C11.148 (3)C10—C111.373 (3)
N2—C81.135 (3)C11—C121.396 (3)
C1—C21.430 (4)C11—H110.9300
C2—C31.385 (3)C12—C131.388 (4)
C2—C71.391 (3)C12—H120.9300
C3—C41.377 (3)C13—C141.372 (4)
C3—H30.9300C13—H130.9300
C4—C51.380 (3)C14—C151.381 (4)
C4—H40.9300C14—H140.9300
C5—C61.384 (3)C15—C161.503 (3)
C6—C71.387 (3)C16—C171.525 (3)
C6—H60.9300C16—H16A0.9700
C7—C81.452 (3)C16—H16B0.9700
C9—C101.500 (3)C17—H17A0.9700
C9—C171.529 (3)C17—H17B0.9700
C5—O1—C9117.8 (2)C11—C10—C9127.2 (3)
N1—C1—C2179.0 (4)C10—C11—C12118.1 (3)
C3—C2—C7118.6 (3)C10—C11—H11120.9
C3—C2—C1120.8 (3)C12—C11—H11120.9
C7—C2—C1120.6 (3)C13—C12—C11120.0 (3)
C4—C3—C2120.4 (3)C13—C12—H12120.0
C4—C3—H3119.8C11—C12—H12120.0
C2—C3—H3119.8C14—C13—C12120.9 (3)
C3—C4—C5120.5 (3)C14—C13—H13119.5
C3—C4—H4119.7C12—C13—H13119.5
C5—C4—H4119.7C13—C14—C15118.6 (3)
O1—C5—C4115.5 (3)C13—C14—H14120.7
O1—C5—C6124.2 (3)C15—C14—H14120.7
C4—C5—C6120.3 (3)C10—C15—C14120.7 (3)
C7—C6—C5118.8 (3)C10—C15—C16111.0 (3)
C7—C6—H6120.6C14—C15—C16128.3 (3)
C5—C6—H6120.6C15—C16—C17104.3 (2)
C6—C7—C2121.4 (3)C15—C16—H16A110.9
C6—C7—C8118.3 (3)C17—C16—H16A110.9
C2—C7—C8120.3 (3)C15—C16—H16B110.9
N2—C8—C7178.0 (3)C17—C16—H16B110.9
O1—C9—C10109.0 (2)H16A—C16—H16B108.9
O1—C9—C17113.1 (2)C16—C17—C9106.5 (2)
C10—C9—C17104.1 (2)C16—C17—H17A110.4
O1—C9—H9110.2C9—C17—H17A110.4
C10—C9—H9110.2C16—C17—H17B110.4
C17—C9—H9110.2C9—C17—H17B110.4
C15—C10—C11121.6 (3)H17A—C17—H17B108.6
C15—C10—C9111.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···Cg3i0.982.693.625 (4)160
C17—H17A···Cg3ii0.972.993.917 (4)160
Symmetry codes: (i) x+1, y, z+2; (ii) x, y, z+2.
 

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