4-(2-Iso­propyl-5-methyl­phenoxy)­phthalo­nitrile

In the title compound, C₁₈H₁₆N₂O, two benzene rings are connected by an O atom, and the dihedral angle between them is 86.83 (1)°. The C-O-C angle is 118.50 (14)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.062
• wR factor = 0.219
• Data-to-parameter ratio = 21.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C1     -   C7       =       1.43 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C2     -   C8       =       1.44 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

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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) and PARST (Nardelli, 1995).

4-[2-Isopropyl-5-methylphenoxy]phthalonitrile

Crystal data

C18H16N2O	F(000) = 584
Mr = 276.33	Dx = 1.177 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15187 reflections
a = 11.424 (2) Å	θ = 1.8–29.4°
b = 10.2230 (12) Å	µ = 0.07 mm^−1
c = 13.669 (2) Å	T = 293 K
β = 102.406 (1)°	Tetragonal, light brown
V = 1559.1 (4) Å^3	0.40 × 0.33 × 0.30 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	2185 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 29.5°, θmin = 2.1°
ω scans	h = −15→15
14570 measured reflections	k = −13→14
4223 independent reflections	l = −16→18

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.219	H-atom parameters constrained
S = 0.88	w = 1/[σ^2(Fo^2) + (0.1493P)^2] where P = (Fo^2 + 2Fc^2)/3
4223 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.21 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
N2	0.6548 (3)	0.5094 (2)	0.1058 (2)	0.1241 (10)
N1	0.76274 (17)	0.34011 (18)	0.36416 (15)	0.0833 (6)
C7	0.6179 (2)	0.4084 (2)	0.11874 (17)	0.0826 (6)
C15	0.2330 (5)	0.0914 (5)	0.3733 (4)	0.194 (2)
H15A	0.1891	0.0462	0.4155	0.291*
H15B	0.1858	0.1629	0.3405	0.291*
H15C	0.3066	0.1244	0.4132	0.291*
C8	0.69444 (15)	0.28661 (18)	0.30523 (13)	0.0594 (4)
C1	0.57186 (16)	0.28233 (18)	0.13556 (14)	0.0615 (5)
C2	0.60824 (14)	0.22191 (16)	0.22845 (12)	0.0530 (4)
C16	0.2591 (2)	0.0027 (3)	0.2994 (2)	0.0984 (8)
H16	0.2895	0.0579	0.2518	0.118*
C6	0.48739 (18)	0.2201 (2)	0.06171 (14)	0.0718 (5)
H6	0.4624	0.2590	−0.0008	0.086*
C17	0.1512 (3)	−0.0643 (4)	0.2387 (3)	0.1410 (14)
H17A	0.1233	−0.1292	0.2790	0.211*
H17B	0.1721	−0.1056	0.1817	0.211*
H17C	0.0891	−0.0011	0.2163	0.211*
C3	0.56191 (15)	0.10200 (17)	0.24792 (13)	0.0580 (4)
H3	0.5869	0.0620	0.3100	0.070*
C5	0.44112 (18)	0.1019 (2)	0.08071 (14)	0.0707 (5)
H5	0.3846	0.0608	0.0311	0.085*
C13	0.3730 (2)	−0.1582 (2)	0.42912 (19)	0.0856 (7)
H13	0.3202	−0.1400	0.4704	0.103*
C14	0.35844 (19)	−0.0944 (2)	0.33776 (17)	0.0744 (6)
C4	0.47796 (16)	0.04311 (18)	0.17336 (14)	0.0619 (5)
C12	0.4636 (2)	−0.2480 (2)	0.46065 (18)	0.0834 (6)
H12	0.4700	−0.2889	0.5223	0.100*
C9	0.44028 (18)	−0.12750 (18)	0.28159 (15)	0.0663 (5)
O1	0.42601 (15)	−0.07445 (14)	0.18432 (11)	0.0864 (5)
C11	0.54423 (19)	−0.27788 (19)	0.40285 (17)	0.0740 (6)
C10	0.52993 (19)	−0.2153 (2)	0.31139 (17)	0.0722 (5)
H10	0.5824	−0.2337	0.2698	0.087*
C18	0.6433 (3)	−0.3754 (3)	0.4379 (3)	0.1084 (9)
H18A	0.6729	−0.4064	0.3815	0.163*
H18B	0.6128	−0.4477	0.4697	0.163*
H18C	0.7072	−0.3341	0.4849	0.163*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2	0.142 (2)	0.0912 (15)	0.122 (2)	−0.0458 (15)	−0.0087 (16)	0.0321 (14)
N1	0.0832 (11)	0.0768 (11)	0.0770 (12)	−0.0089 (9)	−0.0112 (9)	−0.0111 (9)
C7	0.0892 (14)	0.0757 (13)	0.0726 (13)	−0.0170 (11)	−0.0054 (11)	0.0171 (10)
C15	0.219 (5)	0.150 (3)	0.175 (4)	0.111 (3)	−0.043 (3)	−0.055 (3)
C8	0.0591 (9)	0.0576 (9)	0.0570 (10)	−0.0016 (8)	0.0026 (7)	0.0001 (8)
C1	0.0619 (10)	0.0600 (10)	0.0591 (10)	−0.0066 (8)	0.0051 (8)	0.0085 (8)
C2	0.0500 (8)	0.0543 (9)	0.0516 (9)	−0.0015 (6)	0.0038 (6)	−0.0015 (7)
C16	0.0876 (15)	0.0929 (17)	0.108 (2)	0.0156 (13)	0.0053 (14)	0.0089 (15)
C6	0.0780 (12)	0.0762 (12)	0.0523 (10)	−0.0107 (10)	−0.0055 (8)	0.0144 (9)
C17	0.0871 (18)	0.130 (3)	0.182 (4)	0.0098 (18)	−0.024 (2)	−0.006 (3)
C3	0.0601 (9)	0.0578 (9)	0.0509 (9)	−0.0039 (7)	0.0000 (7)	0.0052 (7)
C5	0.0757 (12)	0.0737 (12)	0.0530 (10)	−0.0145 (9)	−0.0081 (8)	0.0023 (8)
C13	0.0829 (14)	0.0931 (16)	0.0837 (15)	0.0065 (12)	0.0244 (11)	0.0051 (12)
C14	0.0747 (12)	0.0642 (11)	0.0766 (13)	0.0007 (9)	−0.0006 (10)	0.0032 (9)
C4	0.0673 (10)	0.0571 (9)	0.0563 (10)	−0.0122 (8)	0.0017 (8)	0.0033 (7)
C12	0.0907 (15)	0.0812 (14)	0.0781 (14)	0.0036 (11)	0.0175 (11)	0.0232 (11)
C9	0.0776 (12)	0.0536 (9)	0.0624 (11)	−0.0159 (8)	0.0032 (9)	0.0035 (8)
O1	0.1072 (11)	0.0739 (9)	0.0659 (9)	−0.0380 (8)	−0.0086 (7)	0.0086 (7)
C11	0.0775 (12)	0.0558 (10)	0.0861 (14)	−0.0004 (9)	0.0115 (10)	0.0078 (9)
C10	0.0718 (11)	0.0660 (11)	0.0790 (13)	−0.0106 (9)	0.0167 (9)	0.0006 (10)
C18	0.1065 (19)	0.0802 (15)	0.135 (3)	0.0255 (14)	0.0173 (17)	0.0168 (16)

Geometric parameters (Å, º)

N2—C7	1.144 (3)	C3—C4	1.379 (2)
N1—C8	1.134 (2)	C3—H3	0.9300
C7—C1	1.429 (3)	C5—C4	1.383 (3)
C15—C16	1.434 (5)	C5—H5	0.9300
C15—H15A	0.9600	C13—C12	1.381 (3)
C15—H15B	0.9600	C13—C14	1.387 (3)
C15—H15C	0.9600	C13—H13	0.9300
C8—C2	1.437 (2)	C14—C9	1.373 (3)
C1—C6	1.392 (3)	C4—O1	1.363 (2)
C1—C2	1.393 (2)	C12—C11	1.371 (3)
C2—C3	1.384 (2)	C12—H12	0.9300
C16—C17	1.496 (4)	C9—C10	1.357 (3)
C16—C14	1.514 (3)	C9—O1	1.413 (2)
C16—H16	0.9800	C11—C10	1.382 (3)
C6—C5	1.366 (3)	C11—C18	1.507 (3)
C6—H6	0.9300	C10—H10	0.9300
C17—H17A	0.9600	C18—H18A	0.9600
C17—H17B	0.9600	C18—H18B	0.9600
C17—H17C	0.9600	C18—H18C	0.9600
N2—C7—C1	179.7 (3)	C6—C5—C4	120.30 (17)
C16—C15—H15A	109.5	C6—C5—H5	119.9
C16—C15—H15B	109.5	C4—C5—H5	119.9
H15A—C15—H15B	109.5	C12—C13—C14	122.1 (2)
C16—C15—H15C	109.5	C12—C13—H13	119.0
H15A—C15—H15C	109.5	C14—C13—H13	119.0
H15B—C15—H15C	109.5	C9—C14—C13	115.02 (19)
N1—C8—C2	178.3 (2)	C9—C14—C16	121.2 (2)
C6—C1—C2	118.89 (16)	C13—C14—C16	123.8 (2)
C6—C1—C7	121.16 (17)	O1—C4—C3	123.64 (16)
C2—C1—C7	119.91 (16)	O1—C4—C5	115.46 (15)
C3—C2—C1	121.12 (14)	C3—C4—C5	120.90 (17)
C3—C2—C8	119.85 (15)	C11—C12—C13	121.3 (2)
C1—C2—C8	119.03 (15)	C11—C12—H12	119.3
C15—C16—C17	114.2 (3)	C13—C12—H12	119.3
C15—C16—C14	115.1 (3)	C10—C9—C14	123.75 (19)
C17—C16—C14	111.0 (2)	C10—C9—O1	117.62 (19)
C15—C16—H16	105.1	C14—C9—O1	118.48 (19)
C17—C16—H16	105.1	C4—O1—C9	118.50 (14)
C14—C16—H16	105.1	C12—C11—C10	117.0 (2)
C5—C6—C1	120.19 (17)	C12—C11—C18	121.1 (2)
C5—C6—H6	119.9	C10—C11—C18	121.9 (2)
C1—C6—H6	119.9	C9—C10—C11	120.8 (2)
C16—C17—H17A	109.5	C9—C10—H10	119.6
C16—C17—H17B	109.5	C11—C10—H10	119.6
H17A—C17—H17B	109.5	C11—C18—H18A	109.5
C16—C17—H17C	109.5	C11—C18—H18B	109.5
H17A—C17—H17C	109.5	H18A—C18—H18B	109.5
H17B—C17—H17C	109.5	C11—C18—H18C	109.5
C4—C3—C2	118.60 (15)	H18A—C18—H18C	109.5
C4—C3—H3	120.7	H18B—C18—H18C	109.5
C2—C3—H3	120.7
C6—C1—C2—C3	0.0 (3)	C6—C5—C4—O1	179.9 (2)
C7—C1—C2—C3	177.68 (19)	C6—C5—C4—C3	−0.2 (3)
C6—C1—C2—C8	−179.31 (18)	C14—C13—C12—C11	0.3 (4)
C7—C1—C2—C8	−1.6 (3)	C13—C14—C9—C10	−0.2 (3)
C2—C1—C6—C5	0.2 (3)	C16—C14—C9—C10	−178.9 (2)
C7—C1—C6—C5	−177.4 (2)	C13—C14—C9—O1	175.19 (17)
C1—C2—C3—C4	−0.3 (3)	C16—C14—C9—O1	−3.5 (3)
C8—C2—C3—C4	179.01 (17)	C3—C4—O1—C9	12.7 (3)
C1—C6—C5—C4	−0.1 (3)	C5—C4—O1—C9	−167.41 (19)
C12—C13—C14—C9	0.2 (3)	C10—C9—O1—C4	−95.7 (2)
C12—C13—C14—C16	178.8 (2)	C14—C9—O1—C4	88.6 (2)
C15—C16—C14—C9	−140.6 (4)	C13—C12—C11—C10	−0.7 (3)
C17—C16—C14—C9	87.8 (3)	C13—C12—C11—C18	179.7 (2)
C15—C16—C14—C13	40.8 (5)	C14—C9—C10—C11	−0.2 (3)
C17—C16—C14—C13	−90.8 (3)	O1—C9—C10—C11	−175.62 (17)
C2—C3—C4—O1	−179.71 (18)	C12—C11—C10—C9	0.6 (3)
C2—C3—C4—C5	0.4 (3)	C18—C11—C10—C9	−179.8 (2)