4-(2,3,5-Trimethyl­phen­oxy)phthalonitrile

The crystal structure of the title compound, C₁₇H₁₄N₂O, is stabilized by weak van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](Wave) = 0.000 Å
• R factor = 0.036
• wR factor = 0.100
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 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
   0 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
   0 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-RED32 (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) and PARST (Nardelli, 1995).

4-(2,3,5-Trimethylphenoxy)phthalonitrile

Crystal data

C17H14N2O	F(000) = 1104
Mr = 262.30	Dx = 1.204 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 10756 reflections
a = 7.8929 (8) Å	θ = 1.4–26.0°
b = 29.415 (4) Å	µ = 0.08 mm^−1
c = 12.4679 (14) Å	T = 293 K
V = 2894.7 (6) Å^3	Prism, colourless
Z = 8	0.38 × 0.20 × 0.20 mm

Data collection

Stoe IPDS-2 diffractometer	2841 independent reflections
Radiation source: fine-focus sealed tube	1343 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
ω scans	θmax = 26.0°, θmin = 1.4°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.926, Tmax = 0.970	k = −36→36
15698 measured reflections	l = −15→14

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.056P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max = 0.001
2841 reflections	Δρmax = 0.09 e Å^−3
205 parameters	Δρmin = −0.10 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (6)

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
H3	0.427 (2)	0.2576 (6)	0.9789 (13)	0.078 (5)*
H6	0.089 (2)	0.3840 (6)	1.0526 (13)	0.083 (5)*
H4	0.278 (2)	0.2934 (6)	0.8401 (15)	0.098 (6)*
H10	0.172 (3)	0.4427 (6)	0.8267 (14)	0.085 (6)*
H12	−0.270 (2)	0.4973 (7)	0.9005 (14)	0.090 (7)*
O1	0.08617 (16)	0.35993 (4)	0.84833 (8)	0.0852 (4)
C10	0.0513 (3)	0.44001 (6)	0.84694 (13)	0.0745 (5)
C9	−0.0183 (2)	0.39806 (6)	0.86624 (12)	0.0701 (5)
C11	−0.0455 (3)	0.47838 (6)	0.85891 (13)	0.0791 (5)
C7	0.2486 (2)	0.33806 (6)	1.11797 (12)	0.0675 (5)
C2	0.3498 (2)	0.30027 (6)	1.09748 (12)	0.0665 (5)
C6	0.1570 (2)	0.35856 (6)	1.03733 (13)	0.0715 (5)
C5	0.1695 (2)	0.34164 (6)	0.93371 (12)	0.0685 (5)
C1	0.4413 (2)	0.27873 (6)	1.18280 (15)	0.0744 (5)
C14	−0.1837 (3)	0.39120 (6)	0.89720 (12)	0.0746 (5)
C13	−0.2811 (3)	0.42981 (8)	0.91191 (13)	0.0829 (6)
C8	0.2392 (2)	0.35666 (6)	1.22459 (15)	0.0806 (5)
C3	0.3594 (2)	0.28369 (7)	0.99302 (14)	0.0739 (5)
C12	−0.2121 (3)	0.47217 (8)	0.89229 (14)	0.0853 (6)
N1	0.5126 (2)	0.26150 (5)	1.25134 (14)	0.0933 (5)
C4	0.2706 (2)	0.30446 (6)	0.91223 (14)	0.0751 (5)
C15	0.0247 (3)	0.52510 (6)	0.83666 (16)	0.1115 (8)
H15A	0.0496	0.5400	0.9033	0.167*
H15B	−0.0574	0.5426	0.7975	0.167*
H15C	0.1265	0.5225	0.7950	0.167*
N2	0.2328 (3)	0.37180 (6)	1.30813 (14)	0.1127 (6)
C17	−0.2528 (3)	0.34413 (7)	0.91417 (15)	0.1031 (7)
H17A	−0.1737	0.3222	0.8869	0.155*
H17B	−0.3588	0.3411	0.8770	0.155*
H17C	−0.2700	0.3390	0.9894	0.155*
C16	−0.4652 (3)	0.42626 (9)	0.94664 (19)	0.1253 (8)
H16A	−0.5270	0.4084	0.8953	0.188*
H16B	−0.5137	0.4561	0.9508	0.188*
H16C	−0.4712	0.4119	1.0157	0.188*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1135 (10)	0.0888 (8)	0.0533 (7)	0.0225 (8)	−0.0006 (6)	−0.0015 (6)
C10	0.0820 (14)	0.0842 (14)	0.0571 (10)	−0.0006 (12)	−0.0004 (9)	0.0054 (9)
C9	0.0869 (14)	0.0766 (11)	0.0468 (9)	0.0117 (11)	−0.0022 (8)	−0.0001 (8)
C11	0.1035 (16)	0.0785 (12)	0.0552 (10)	0.0018 (12)	−0.0042 (10)	0.0030 (8)
C7	0.0808 (12)	0.0677 (10)	0.0540 (9)	−0.0018 (10)	0.0020 (9)	0.0011 (8)
C2	0.0703 (11)	0.0652 (10)	0.0642 (10)	−0.0037 (9)	0.0012 (9)	0.0044 (8)
C6	0.0880 (13)	0.0681 (11)	0.0585 (11)	0.0077 (10)	0.0048 (9)	−0.0022 (8)
C5	0.0841 (12)	0.0675 (11)	0.0538 (10)	0.0047 (9)	0.0032 (9)	−0.0005 (8)
C1	0.0762 (12)	0.0720 (11)	0.0751 (12)	−0.0043 (10)	0.0011 (10)	0.0050 (9)
C14	0.0847 (14)	0.0861 (13)	0.0530 (10)	−0.0008 (11)	−0.0043 (9)	0.0044 (8)
C13	0.0806 (15)	0.1086 (16)	0.0597 (11)	0.0021 (12)	−0.0057 (9)	0.0058 (10)
C8	0.1007 (15)	0.0783 (11)	0.0628 (11)	0.0054 (11)	−0.0023 (10)	0.0004 (9)
C3	0.0808 (13)	0.0685 (11)	0.0724 (12)	0.0071 (10)	0.0076 (10)	−0.0021 (9)
C12	0.1003 (19)	0.0925 (16)	0.0630 (11)	0.0273 (14)	−0.0044 (11)	−0.0015 (10)
N1	0.0936 (13)	0.0955 (11)	0.0909 (11)	−0.0019 (10)	−0.0123 (10)	0.0145 (9)
C4	0.0892 (14)	0.0739 (12)	0.0624 (11)	0.0052 (10)	0.0082 (10)	−0.0067 (9)
C15	0.165 (2)	0.0799 (13)	0.0901 (14)	−0.0095 (14)	−0.0007 (15)	0.0051 (10)
N2	0.1631 (19)	0.1066 (13)	0.0683 (11)	0.0037 (12)	−0.0069 (11)	−0.0118 (9)
C17	0.1271 (19)	0.1032 (15)	0.0788 (13)	−0.0274 (14)	−0.0029 (12)	0.0075 (11)
C16	0.0824 (16)	0.179 (2)	0.1143 (18)	0.0091 (16)	0.0115 (13)	0.0172 (16)

Geometric parameters (Å, º)

O1—C5	1.3621 (19)	C14—C17	1.503 (3)
O1—C9	1.4097 (19)	C13—C12	1.381 (3)
C10—C11	1.371 (2)	C13—C16	1.520 (3)
C10—C9	1.372 (2)	C8—N2	1.134 (2)
C10—H10	0.991 (19)	C3—C4	1.371 (2)
C9—C14	1.376 (2)	C3—H3	0.953 (17)
C11—C12	1.392 (3)	C12—H12	0.877 (19)
C11—C15	1.507 (2)	C4—H4	0.958 (19)
C7—C6	1.377 (2)	C15—H15A	0.9600
C7—C2	1.393 (2)	C15—H15B	0.9600
C7—C8	1.439 (2)	C15—H15C	0.9600
C2—C3	1.393 (2)	C17—H17A	0.9600
C2—C1	1.433 (3)	C17—H17B	0.9600
C6—C5	1.388 (2)	C17—H17C	0.9600
C6—H6	0.942 (17)	C16—H16A	0.9600
C5—C4	1.380 (2)	C16—H16B	0.9600
C1—N1	1.142 (2)	C16—H16C	0.9600
C14—C13	1.384 (3)
C5—O1—C9	118.22 (12)	N2—C8—C7	179.1 (2)
C11—C10—C9	119.9 (2)	C4—C3—C2	120.23 (19)
C11—C10—H10	119.9 (10)	C4—C3—H3	120.7 (10)
C9—C10—H10	120.1 (10)	C2—C3—H3	119.0 (10)
C10—C9—C14	124.10 (17)	C13—C12—C11	123.0 (2)
C10—C9—O1	117.00 (18)	C13—C12—H12	122.2 (13)
C14—C9—O1	118.84 (16)	C11—C12—H12	114.9 (13)
C10—C11—C12	116.8 (2)	C3—C4—C5	120.41 (17)
C10—C11—C15	121.8 (2)	C3—C4—H4	120.3 (11)
C12—C11—C15	121.45 (19)	C5—C4—H4	119.2 (11)
C6—C7—C2	121.11 (15)	C11—C15—H15A	109.5
C6—C7—C8	118.74 (16)	C11—C15—H15B	109.5
C2—C7—C8	120.15 (15)	H15A—C15—H15B	109.5
C3—C2—C7	118.82 (16)	C11—C15—H15C	109.5
C3—C2—C1	120.81 (17)	H15A—C15—H15C	109.5
C7—C2—C1	120.37 (15)	H15B—C15—H15C	109.5
C7—C6—C5	119.02 (17)	C14—C17—H17A	109.5
C7—C6—H6	120.1 (10)	C14—C17—H17B	109.5
C5—C6—H6	120.9 (10)	H17A—C17—H17B	109.5
O1—C5—C4	116.14 (14)	C14—C17—H17C	109.5
O1—C5—C6	123.46 (16)	H17A—C17—H17C	109.5
C4—C5—C6	120.39 (17)	H17B—C17—H17C	109.5
N1—C1—C2	179.3 (2)	C13—C16—H16A	109.5
C9—C14—C13	116.35 (18)	C13—C16—H16B	109.5
C9—C14—C17	121.26 (18)	H16A—C16—H16B	109.5
C13—C14—C17	122.4 (2)	C13—C16—H16C	109.5
C12—C13—C14	119.8 (2)	H16A—C16—H16C	109.5
C12—C13—C16	119.3 (2)	H16B—C16—H16C	109.5
C14—C13—C16	120.8 (2)
C11—C10—C9—C14	0.4 (2)	O1—C9—C14—C13	−178.96 (14)
C11—C10—C9—O1	177.56 (14)	C10—C9—C14—C17	178.36 (16)
C5—O1—C9—C10	96.19 (18)	O1—C9—C14—C17	1.2 (2)
C5—O1—C9—C14	−86.49 (19)	C9—C14—C13—C12	2.0 (2)
C9—C10—C11—C12	0.9 (2)	C17—C14—C13—C12	−178.24 (15)
C9—C10—C11—C15	−178.88 (16)	C9—C14—C13—C16	−179.67 (16)
C6—C7—C2—C3	0.9 (3)	C17—C14—C13—C16	0.1 (3)
C8—C7—C2—C3	−178.54 (16)	C7—C2—C3—C4	0.2 (3)
C6—C7—C2—C1	−178.58 (16)	C1—C2—C3—C4	179.67 (17)
C8—C7—C2—C1	1.9 (2)	C14—C13—C12—C11	−0.8 (3)
C2—C7—C6—C5	−1.4 (3)	C16—C13—C12—C11	−179.15 (17)
C8—C7—C6—C5	178.06 (17)	C10—C11—C12—C13	−0.7 (3)
C9—O1—C5—C4	−179.81 (16)	C15—C11—C12—C13	179.06 (17)
C9—O1—C5—C6	0.0 (3)	C2—C3—C4—C5	−0.7 (3)
C7—C6—C5—O1	−178.96 (16)	O1—C5—C4—C3	−179.94 (17)
C7—C6—C5—C4	0.8 (3)	C6—C5—C4—C3	0.2 (3)
C10—C9—C14—C13	−1.9 (2)