4-(2-Allyl­phenoxy)­phthalo­nitrile

In the title compound, C₁₇H₁₂N₂O, the mutual orientation of the two aromatic rings [dihedral angle 80.8 (1)°] is mainly determined by the presence of an intramolecular C—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.058
• wR factor = 0.178
• Data-to-parameter ratio = 9.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



DIFMX_01  Alert C The maximum difference density is > 0.1*ZMAX*0.75
          _refine_diff_density_max given =      0.716
          Test value =      0.600

DIFMX_02  Alert C The minimum difference density is > 0.1*ZMAX*0.75
          The relevant atom site should be identified.

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.74
         From the CIF: _reflns_number_total               1777
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         1889
         Completeness (_total/calc)             94.07%
          Alert C: < 95% complete

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C7     -   C14      =       1.44 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C12    -   C13      =       1.44 Ang.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         29
                   C11 -C12 -C13 -N1    167.00  9.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
                   C7  -C12 -C13 -N1    -13.00  9.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
                   C12 -C7  -C14 -N2    -85.00  9.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
                   C8  -C7  -C14 -N2     92.00  9.00   1.555   1.555   1.555   1.555

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.74
         From the CIF: _reflns_number_total               1777
         Count of symmetry unique reflns         1889
         Completeness (_total/calc)             94.07%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 9 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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) and PARST (Nardelli, 1995).

4-(2-Allylphenoxy)phthalonitrile

Crystal data

C17H12N2O	Dx = 1.258 Mg m^−3
Mr = 260.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 10384 reflections
a = 14.1639 (14) Å	θ = 2.3–28.7°
b = 11.2630 (11) Å	µ = 0.08 mm^−1
c = 8.6098 (8) Å	T = 150 K
V = 1373.5 (2) Å^3	Block, green
Z = 4	0.31 × 0.25 × 0.11 mm
F(000) = 544

Data collection

Bruker CCD area-detector diffractometer	1777 independent reflections
Radiation source: sealed tube	1468 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 28.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→15
Tmin = 0.975, Tmax = 0.991	k = −14→14
9839 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.178	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1037P)^2 + 0.3289P] where P = (Fo^2 + 2Fc^2)/3
1777 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.72 e Å^−3
1 restraint	Δρmin = −0.38 e Å^−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
O1	0.00062 (19)	0.9665 (3)	0.3276 (3)	0.0680 (10)
N1	−0.1290 (2)	0.6821 (3)	0.8664 (4)	0.0566 (9)
N2	−0.3779 (2)	0.8041 (3)	0.7409 (4)	0.0570 (8)
C1	0.0937 (2)	0.9295 (3)	0.3524 (4)	0.0454 (8)
C2	0.1312 (3)	0.8451 (3)	0.2547 (5)	0.0562 (10)
C3	0.2269 (4)	0.8242 (4)	0.2694 (6)	0.0680 (13)
H3	0.2556	0.7693	0.2038	0.082*
C4	0.2813 (3)	0.8825 (5)	0.3787 (7)	0.0728 (15)
H4	0.3456	0.8669	0.3852	0.087*
C5	0.2408 (3)	0.9636 (4)	0.4780 (6)	0.0637 (11)
H5	0.2767	1.0015	0.5536	0.076*
C6	0.1454 (3)	0.9874 (4)	0.4626 (5)	0.0540 (9)
H6	0.1167	1.0427	0.5273	0.065*
C7	−0.2278 (2)	0.8753 (2)	0.5997 (3)	0.0337 (6)
C8	−0.2348 (2)	0.9579 (3)	0.4795 (4)	0.0394 (7)
H8	−0.2927	0.9929	0.4571	0.047*
C9	−0.1563 (2)	0.9877 (3)	0.3940 (4)	0.0427 (7)
H9	−0.1612	1.0435	0.3147	0.051*
C10	−0.0702 (2)	0.9355 (3)	0.4253 (4)	0.0402 (7)
C11	−0.0599 (2)	0.8561 (2)	0.5487 (3)	0.0345 (6)
H11	−0.0013	0.8238	0.5728	0.041*
C12	−0.1394 (2)	0.8267 (2)	0.6341 (4)	0.0334 (6)
C13	−0.1319 (2)	0.7454 (3)	0.7627 (4)	0.0391 (7)
C14	−0.3113 (2)	0.8375 (3)	0.6806 (4)	0.0425 (7)
C15	0.0744 (6)	0.7811 (4)	0.1316 (8)	0.100 (2)
H15A	0.0214	0.8310	0.1025	0.120*
H15B	0.1137	0.7713	0.0403	0.120*
C16	0.0371 (5)	0.6617 (4)	0.1777 (9)	0.0871 (18)
H16	0.0054	0.6206	0.0999	0.104*
C17	0.0422 (4)	0.6098 (5)	0.3042 (8)	0.0832 (16)
H17A	0.0728	0.6457	0.3874	0.100*
H17B	0.0154	0.5350	0.3159	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0394 (14)	0.108 (3)	0.0566 (18)	0.0083 (14)	0.0076 (13)	0.0453 (18)
N1	0.0470 (17)	0.0600 (17)	0.063 (2)	−0.0046 (14)	−0.0016 (16)	0.0265 (17)
N2	0.0377 (15)	0.072 (2)	0.062 (2)	−0.0062 (14)	0.0061 (15)	0.0066 (17)
C1	0.0392 (17)	0.0536 (18)	0.0434 (17)	−0.0014 (14)	0.0071 (15)	0.0189 (15)
C2	0.082 (3)	0.0440 (17)	0.0430 (19)	0.0031 (17)	−0.0030 (19)	0.0125 (16)
C3	0.081 (3)	0.063 (2)	0.060 (2)	0.030 (2)	0.018 (2)	0.024 (2)
C4	0.0383 (19)	0.091 (3)	0.089 (4)	0.011 (2)	0.011 (2)	0.055 (3)
C5	0.053 (2)	0.074 (2)	0.064 (3)	−0.0108 (19)	−0.010 (2)	0.024 (2)
C6	0.064 (2)	0.056 (2)	0.0423 (19)	0.0059 (17)	−0.0001 (17)	0.0080 (17)
C7	0.0343 (15)	0.0351 (13)	0.0318 (14)	−0.0032 (11)	−0.0010 (11)	−0.0041 (11)
C8	0.0394 (17)	0.0401 (14)	0.0386 (16)	0.0054 (12)	−0.0030 (14)	0.0002 (13)
C9	0.0429 (18)	0.0491 (17)	0.0359 (16)	0.0018 (14)	−0.0032 (13)	0.0076 (14)
C10	0.0388 (16)	0.0496 (16)	0.0322 (14)	−0.0003 (13)	0.0020 (13)	0.0079 (13)
C11	0.0330 (15)	0.0398 (13)	0.0309 (14)	−0.0004 (11)	−0.0027 (11)	0.0045 (12)
C12	0.0355 (15)	0.0321 (13)	0.0326 (13)	−0.0036 (11)	−0.0020 (11)	0.0000 (11)
C13	0.0319 (14)	0.0421 (14)	0.0431 (16)	−0.0022 (12)	−0.0003 (13)	0.0071 (14)
C14	0.0356 (17)	0.0462 (16)	0.0457 (18)	−0.0003 (12)	−0.0027 (15)	−0.0009 (15)
C15	0.165 (6)	0.049 (2)	0.085 (4)	−0.002 (3)	−0.052 (4)	0.005 (2)
C16	0.099 (4)	0.054 (2)	0.109 (5)	0.008 (2)	−0.023 (4)	−0.011 (3)
C17	0.058 (3)	0.094 (4)	0.098 (4)	0.004 (3)	−0.007 (3)	−0.003 (3)

Geometric parameters (Å, º)

O1—C10	1.355 (4)	C7—C14	1.437 (5)
O1—C1	1.399 (4)	C8—C9	1.375 (5)
N1—C13	1.144 (5)	C8—H8	0.9300
N2—C14	1.141 (5)	C9—C10	1.380 (5)
C1—C6	1.365 (6)	C9—H9	0.9300
C1—C2	1.377 (6)	C10—C11	1.397 (4)
C2—C3	1.382 (7)	C11—C12	1.385 (4)
C2—C15	1.513 (7)	C11—H11	0.9300
C3—C4	1.382 (8)	C12—C13	1.440 (4)
C3—H3	0.9300	C15—C16	1.498 (7)
C4—C5	1.375 (8)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.383 (6)	C16—C17	1.238 (9)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—H17A	0.9300
C7—C12	1.397 (4)	C17—H17B	0.9300
C7—C8	1.395 (4)
C10—O1—C1	121.8 (3)	C8—C9—H9	119.8
C6—C1—C2	123.2 (4)	C10—C9—H9	119.8
C6—C1—O1	118.1 (4)	O1—C10—C9	115.1 (3)
C2—C1—O1	118.4 (4)	O1—C10—C11	124.0 (3)
C1—C2—C3	116.1 (4)	C9—C10—C11	120.9 (3)
C1—C2—C15	123.5 (5)	C12—C11—C10	118.2 (3)
C3—C2—C15	120.3 (5)	C12—C11—H11	120.9
C4—C3—C2	121.8 (4)	C10—C11—H11	120.9
C4—C3—H3	119.1	C11—C12—C7	121.4 (3)
C2—C3—H3	119.1	C11—C12—C13	120.0 (3)
C5—C4—C3	120.4 (4)	C7—C12—C13	118.6 (3)
C5—C4—H4	119.8	N1—C13—C12	177.6 (4)
C3—C4—H4	119.8	N2—C14—C7	177.4 (4)
C4—C5—C6	118.4 (5)	C16—C15—C2	115.5 (5)
C4—C5—H5	120.8	C16—C15—H15A	108.4
C6—C5—H5	120.8	C2—C15—H15A	108.4
C1—C6—C5	119.9 (4)	C16—C15—H15B	108.4
C1—C6—H6	120.0	C2—C15—H15B	108.4
C5—C6—H6	120.0	H15A—C15—H15B	107.5
C12—C7—C8	118.9 (3)	C17—C16—C15	129.5 (6)
C12—C7—C14	121.2 (3)	C17—C16—H16	115.2
C8—C7—C14	119.9 (3)	C15—C16—H16	115.2
C9—C8—C7	120.1 (3)	C16—C17—H17A	120.0
C9—C8—H8	119.9	C16—C17—H17B	120.0
C7—C8—H8	119.9	H17A—C17—H17B	120.0
C8—C9—C10	120.4 (3)
C10—O1—C1—C6	−77.8 (5)	C8—C9—C10—O1	176.2 (3)
C10—O1—C1—C2	108.5 (4)	C8—C9—C10—C11	−3.2 (5)
C6—C1—C2—C3	−2.5 (5)	O1—C10—C11—C12	−176.2 (3)
O1—C1—C2—C3	170.9 (3)	C9—C10—C11—C12	3.1 (5)
C6—C1—C2—C15	−179.6 (4)	C10—C11—C12—C7	−0.5 (4)
O1—C1—C2—C15	−6.3 (5)	C10—C11—C12—C13	−179.8 (3)
C1—C2—C3—C4	1.6 (6)	C8—C7—C12—C11	−2.0 (4)
C15—C2—C3—C4	178.9 (4)	C14—C7—C12—C11	175.0 (3)
C2—C3—C4—C5	0.4 (6)	C8—C7—C12—C13	177.3 (3)
C3—C4—C5—C6	−1.8 (6)	C14—C7—C12—C13	−5.7 (4)
C2—C1—C6—C5	1.2 (5)	C11—C12—C13—N1	167 (9)
O1—C1—C6—C5	−172.2 (4)	C7—C12—C13—N1	−13 (9)
C4—C5—C6—C1	1.0 (6)	C12—C7—C14—N2	−85 (9)
C12—C7—C8—C9	1.9 (5)	C8—C7—C14—N2	92 (9)
C14—C7—C8—C9	−175.1 (3)	C1—C2—C15—C16	−96.5 (6)
C7—C8—C9—C10	0.6 (5)	C3—C2—C15—C16	86.5 (7)
C1—O1—C10—C9	174.1 (4)	C2—C15—C16—C17	3.7 (11)
C1—O1—C10—C11	−6.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1^i	0.93	2.53	3.325 (3)	144
C15—H15A···O1	0.97	2.49	2.884 (5)	104

Symmetry code: (i) −x−1/2, y+1/2, z−1/2.