4-(2-Indanoxy)­phthalo­nitrile

In the title mol­ecule, C₁₇H₁₂N₂O, the five-membered ring of the indandione moiety adopts an envelope conformation. The dihedral angle between the 2-indanoxy and phthalo­nitrile groups, excluding the out-of-plane envelope flap atom, is 59.81 (5)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.128
• Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



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 =      0.639
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
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  C14    -   C16      =       1.43 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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); software used to prepare material for publication: WinGX (Farrugia, 1997), PARST (Nardelli, 1995).

4-(2-indanoxy)phthalonitrile

Crystal data

C17H12N2O	F(000) = 544
Mr = 260.30	Dx = 1.298 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 12001 reflections
a = 8.4711 (8) Å	θ = 1.7–0.0°
b = 13.4082 (8) Å	µ = 0.08 mm^−1
c = 11.8736 (11) Å	T = 293 K
β = 99.056 (8)°	Plate, colourless
V = 1331.82 (19) Å^3	0.80 × 0.43 × 0.08 mm
Z = 4

Data collection

STOE IPDS 2 diffractometer	3702 independent reflections
Radiation source: fine-focus sealed tube	1467 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 6.67 pixels mm^-1	θmax = 29.6°, θmin = 1.7°
rotation method scans	h = −11→11
Absorption correction: integration X-RED (Stoe & Cie,2002)	k = 0→18
Tmin = 0.916, Tmax = 0.992	l = 0→16
3702 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0899P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.64	(Δ/σ)max < 0.001
3702 reflections	Δρmax = 0.25 e Å^−3
186 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL-97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (3)

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
H1	0.379 (2)	0.1499 (13)	0.2896 (13)	0.052 (5)*
O1	0.15215 (15)	0.13335 (9)	0.30694 (11)	0.0610 (4)
C3	0.2096 (2)	0.36134 (12)	0.25923 (14)	0.0478 (4)
C15	0.0345 (2)	−0.02255 (12)	0.28340 (14)	0.0504 (4)
H15	−0.0163	−0.0084	0.3455	0.061*
C8	0.24019 (19)	0.35224 (12)	0.37710 (13)	0.0477 (4)
C16	−0.0775 (2)	−0.18986 (14)	0.27722 (15)	0.0570 (5)
C4	0.1388 (2)	0.44649 (13)	0.20891 (15)	0.0564 (4)
H4	0.1177	0.4523	0.1299	0.068*
C14	0.0120 (2)	−0.11439 (12)	0.22954 (14)	0.0498 (4)
C13	0.0840 (2)	−0.13464 (13)	0.13490 (14)	0.0540 (4)
C10	0.13263 (19)	0.04806 (13)	0.24465 (15)	0.0516 (4)
C9	0.3201 (2)	0.25483 (13)	0.41034 (14)	0.0569 (4)
H9A	0.2722	0.2227	0.4699	0.068*
H9B	0.4333	0.2642	0.4371	0.068*
C12	0.1782 (2)	−0.06248 (14)	0.09505 (15)	0.0622 (5)
H12	0.2256	−0.0755	0.0310	0.075*
C5	0.1000 (2)	0.52249 (14)	0.27710 (18)	0.0651 (5)
H5	0.0532	0.5804	0.2440	0.078*
C7	0.1994 (2)	0.42835 (14)	0.44531 (15)	0.0596 (5)
H7	0.2184	0.4225	0.5243	0.072*
C11	0.2026 (2)	0.02861 (14)	0.14937 (16)	0.0604 (5)
H11	0.2659	0.0767	0.1219	0.073*
C1	0.2930 (2)	0.19369 (14)	0.30129 (15)	0.0539 (4)
C2	0.2632 (2)	0.26944 (13)	0.20444 (14)	0.0549 (4)
H2A	0.3602	0.2821	0.1730	0.066*
H2B	0.1810	0.2460	0.1440	0.066*
C17	0.0670 (2)	−0.23072 (15)	0.08071 (15)	0.0638 (5)
C6	0.1296 (2)	0.51368 (15)	0.39364 (18)	0.0677 (5)
H6	0.1024	0.5658	0.4386	0.081*
N1	−0.1454 (2)	−0.25039 (14)	0.31655 (15)	0.0803 (5)
N2	0.0551 (3)	−0.30699 (14)	0.03794 (15)	0.0904 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0559 (8)	0.0459 (7)	0.0848 (8)	−0.0056 (6)	0.0220 (6)	−0.0144 (6)
C3	0.0454 (9)	0.0439 (9)	0.0549 (9)	−0.0053 (7)	0.0102 (7)	−0.0010 (7)
C15	0.0458 (9)	0.0478 (10)	0.0582 (9)	0.0038 (8)	0.0098 (7)	−0.0017 (8)
C8	0.0463 (9)	0.0454 (9)	0.0512 (9)	−0.0062 (8)	0.0070 (7)	−0.0038 (7)
C16	0.0634 (11)	0.0476 (10)	0.0590 (10)	−0.0019 (9)	0.0067 (8)	−0.0002 (8)
C4	0.0570 (10)	0.0520 (11)	0.0606 (10)	−0.0035 (9)	0.0102 (8)	0.0057 (8)
C14	0.0477 (9)	0.0460 (10)	0.0537 (9)	0.0020 (8)	0.0014 (7)	0.0034 (7)
C13	0.0599 (11)	0.0489 (10)	0.0514 (9)	0.0005 (9)	0.0032 (8)	0.0005 (8)
C10	0.0446 (9)	0.0445 (9)	0.0656 (10)	0.0044 (8)	0.0079 (8)	−0.0030 (8)
C9	0.0538 (11)	0.0544 (11)	0.0603 (10)	−0.0003 (8)	0.0021 (8)	0.0008 (8)
C12	0.0733 (13)	0.0574 (12)	0.0581 (10)	0.0012 (10)	0.0172 (9)	−0.0026 (9)
C5	0.0667 (12)	0.0432 (10)	0.0868 (14)	−0.0018 (9)	0.0167 (10)	0.0048 (10)
C7	0.0650 (11)	0.0577 (12)	0.0561 (9)	−0.0096 (10)	0.0092 (8)	−0.0106 (9)
C11	0.0605 (11)	0.0508 (11)	0.0731 (11)	−0.0017 (9)	0.0200 (9)	0.0021 (9)
C1	0.0448 (9)	0.0468 (10)	0.0710 (11)	0.0007 (8)	0.0124 (8)	−0.0016 (8)
C2	0.0559 (10)	0.0542 (11)	0.0554 (9)	−0.0016 (9)	0.0113 (8)	−0.0076 (8)
C17	0.0843 (14)	0.0565 (12)	0.0491 (9)	−0.0046 (10)	0.0062 (9)	−0.0055 (9)
C6	0.0725 (13)	0.0462 (11)	0.0878 (14)	−0.0054 (10)	0.0227 (11)	−0.0166 (10)
N1	0.0946 (14)	0.0621 (11)	0.0858 (12)	−0.0157 (10)	0.0197 (10)	0.0007 (9)
N2	0.1400 (19)	0.0628 (12)	0.0674 (11)	−0.0158 (11)	0.0132 (11)	−0.0163 (9)

Geometric parameters (Å, º)

O1—C10	1.358 (2)	C10—C11	1.382 (2)
O1—C1	1.452 (2)	C9—C1	1.519 (2)
C3—C4	1.381 (2)	C9—H9A	0.9700
C3—C8	1.388 (2)	C9—H9B	0.9700
C3—C2	1.497 (2)	C12—C11	1.381 (3)
C15—C10	1.385 (2)	C12—H12	0.9300
C15—C14	1.387 (2)	C5—C6	1.372 (3)
C15—H15	0.9300	C5—H5	0.9300
C8—C7	1.380 (2)	C7—C6	1.386 (3)
C8—C9	1.495 (2)	C7—H7	0.9300
C16—N1	1.137 (2)	C11—H11	0.9300
C16—C14	1.434 (3)	C1—C2	1.525 (2)
C4—C5	1.373 (3)	C1—H1	0.961 (18)
C4—H4	0.9300	C2—H2A	0.9700
C14—C13	1.387 (2)	C2—H2B	0.9700
C13—C12	1.384 (2)	C17—N2	1.139 (2)
C13—C17	1.437 (3)	C6—H6	0.9300
C10—O1—C1	118.34 (13)	C11—C12—C13	120.68 (17)
C4—C3—C8	120.56 (16)	C11—C12—H12	119.7
C4—C3—C2	129.29 (15)	C13—C12—H12	119.7
C8—C3—C2	110.16 (15)	C6—C5—C4	120.53 (19)
C10—C15—C14	119.98 (16)	C6—C5—H5	119.7
C10—C15—H15	120.0	C4—C5—H5	119.7
C14—C15—H15	120.0	C8—C7—C6	118.65 (17)
C7—C8—C3	120.16 (16)	C8—C7—H7	120.7
C7—C8—C9	129.47 (15)	C6—C7—H7	120.7
C3—C8—C9	110.36 (14)	C12—C11—C10	119.81 (17)
N1—C16—C14	178.4 (2)	C12—C11—H11	120.1
C5—C4—C3	119.10 (17)	C10—C11—H11	120.1
C5—C4—H4	120.4	O1—C1—C9	106.03 (14)
C3—C4—H4	120.4	O1—C1—C2	111.47 (14)
C13—C14—C15	120.10 (16)	C9—C1—C2	105.55 (14)
C13—C14—C16	120.60 (16)	O1—C1—H1	108.1 (10)
C15—C14—C16	119.17 (15)	C9—C1—H1	115.9 (10)
C14—C13—C12	119.39 (16)	C2—C1—H1	109.7 (10)
C14—C13—C17	120.82 (16)	C3—C2—C1	104.25 (13)
C12—C13—C17	119.75 (16)	C3—C2—H2A	110.9
O1—C10—C11	125.01 (16)	C1—C2—H2A	110.9
O1—C10—C15	115.00 (15)	C3—C2—H2B	110.9
C11—C10—C15	119.99 (16)	C1—C2—H2B	110.9
C8—C9—C1	104.19 (14)	H2A—C2—H2B	108.9
C8—C9—H9A	110.9	N2—C17—C13	179.3 (2)
C1—C9—H9A	110.9	C5—C6—C7	121.00 (18)
C8—C9—H9B	110.9	C5—C6—H6	119.5
C1—C9—H9B	110.9	C7—C6—H6	119.5
H9A—C9—H9B	108.9
C4—C3—C8—C7	0.3 (2)	C14—C13—C12—C11	0.8 (3)
C2—C3—C8—C7	−179.59 (15)	C17—C13—C12—C11	−176.76 (18)
C4—C3—C8—C9	−178.78 (15)	C3—C4—C5—C6	−0.6 (3)
C2—C3—C8—C9	1.37 (19)	C3—C8—C7—C6	−0.7 (3)
C8—C3—C4—C5	0.4 (3)	C9—C8—C7—C6	178.09 (17)
C2—C3—C4—C5	−179.74 (17)	C13—C12—C11—C10	0.1 (3)
C10—C15—C14—C13	−1.8 (2)	O1—C10—C11—C12	177.80 (17)
C10—C15—C14—C16	174.15 (16)	C15—C10—C11—C12	−1.9 (3)
C15—C14—C13—C12	0.1 (3)	C10—O1—C1—C9	−156.67 (15)
C16—C14—C13—C12	−175.87 (17)	C10—O1—C1—C2	88.95 (18)
C15—C14—C13—C17	177.59 (16)	C8—C9—C1—O1	−95.56 (15)
C16—C14—C13—C17	1.7 (3)	C8—C9—C1—C2	22.81 (18)
C1—O1—C10—C11	−22.4 (2)	C4—C3—C2—C1	−166.68 (17)
C1—O1—C10—C15	157.30 (15)	C8—C3—C2—C1	13.15 (18)
C14—C15—C10—O1	−176.98 (14)	O1—C1—C2—C3	92.60 (16)
C14—C15—C10—C11	2.8 (3)	C9—C1—C2—C3	−22.07 (18)
C7—C8—C9—C1	165.72 (17)	C4—C5—C6—C7	0.1 (3)
C3—C8—C9—C1	−15.35 (19)	C8—C7—C6—C5	0.6 (3)