3-(4-tert-Butyl­phen­oxy)phthalonitrile

The title compound, C₁₈H₁₆N₂O, contains a phthalonitrile ring lying on a crystallographic mirror plane and a 4-tert-butyl­phen­oxy substituent oriented exactly perpendicular to that plane.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.052
• wR factor = 0.113
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C13

Author Response: The methyl C atoms, C14, C15 of t-butyl group composed of C13, C14 and C15 are disordered with respect to rotation about the C12-C13 single bond. Despite resolving a major and minor disorder component, the U~eq~ values of the methyl C atoms remain high in relation to those of C13.

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.17 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.27 Ratio

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT213_ALERT_2_C Atom C14'    has ADP max/min Ratio .............       3.50 prolat
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9

Author Response: The methyl C atoms, C14, C15 of t-butyl group composed of C13, C14 and C15 are disordered with respect to rotation about the C12-C13 single bond. Despite resolving a major and minor disorder component, the U~eq~ values of the methyl C atoms remain high in relation to those of C13.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12

Author Response: The methyl C atoms, C14, C15 of t-butyl group composed of C13, C14 and C15 are disordered with respect to rotation about the C12-C13 single bond. Despite resolving a major and minor disorder component, the U~eq~ values of the methyl C atoms remain high in relation to those of C13.

PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C3     ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C4     ...       1.43 Ang.

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   8 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
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-(4-tert-Butylphenoxy)phthalonitrile

Crystal data

C18H16N2O	F(000) = 292
Mr = 276.33	Dx = 1.157 Mg m^−3
Monoclinic, P21/m	Melting point = 393–394 K
Hall symbol: -P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 8.7541 (10) Å	Cell parameters from 38 reflections
b = 6.8132 (5) Å	θ = 5.1–12.4°
c = 13.5203 (19) Å	µ = 0.07 mm^−1
β = 100.280 (13)°	T = 295 K
V = 793.45 (16) Å^3	Prism, colorless
Z = 2	0.4 × 0.3 × 0.1 mm

Data collection

Bruker P4 diffractometer	Rint = 0.032
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.4°
Graphite monochromator	h = −1→10
ω scans	k = −1→8
2265 measured reflections	l = −16→16
1621 independent reflections	3 standard reflections every 97 reflections
757 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 0.3P] where P = (Fo^2 + 2Fc^2)/3
1621 reflections	(Δ/σ)max = 0.006
136 parameters	Δρmax = 0.16 e Å^−3
4 restraints	Δρmin = −0.10 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	Occ. (<1)
O1	0.49659 (16)	0.7500	0.74122 (10)	0.0903 (6)
N1	0.8091 (2)	0.7500	0.93367 (17)	0.1123 (9)
N2	0.6044 (3)	0.7500	1.17810 (15)	0.1087 (8)
C1	0.6772 (3)	0.7500	0.92400 (16)	0.0761 (7)
C2	0.5358 (3)	0.7500	1.09817 (17)	0.0822 (8)
C3	0.5126 (2)	0.7500	0.91419 (15)	0.0642 (6)
C4	0.4433 (2)	0.7500	0.99955 (15)	0.0688 (7)
C5	0.2838 (3)	0.7500	0.98960 (17)	0.0808 (8)
H5A	0.2374	0.7500	1.0463	0.097*
C6	0.1934 (3)	0.7500	0.89478 (16)	0.0849 (8)
H6A	0.0858	0.7500	0.8881	0.102*
C7	0.2599 (2)	0.7500	0.81046 (16)	0.0785 (8)
H7A	0.1977	0.7500	0.7470	0.094*
C8	0.4200 (2)	0.7500	0.81993 (16)	0.0685 (7)
C9	0.4086 (2)	0.7500	0.64393 (15)	0.0764 (8)
C10	0.3686 (2)	0.5798 (3)	0.59695 (12)	0.1054 (7)
H10A	0.3972	0.4614	0.6293	0.127*
C11	0.2842 (2)	0.5811 (3)	0.49950 (12)	0.1054 (7)
H11A	0.2577	0.4617	0.4677	0.127*
C12	0.2387 (2)	0.7500	0.44853 (16)	0.0769 (8)
C13	0.1386 (3)	0.7500	0.34446 (17)	0.0905 (9)
C14	0.1654 (5)	0.5741 (6)	0.2820 (2)	0.190 (2)	0.670 (3)
H14A	0.1101	0.5911	0.2146	0.285*	0.670 (3)
H14B	0.1289	0.4580	0.3106	0.285*	0.670 (3)
H14C	0.2744	0.5613	0.2812	0.285*	0.670 (3)
C15	−0.0267 (4)	0.7500	0.3544 (4)	0.211 (4)	0.670 (3)
H15A	−0.0454	0.8612	0.3942	0.316*	0.670 (3)
H15B	−0.0931	0.7500	0.2897	0.316*	0.670 (3)
C14'	0.0334 (9)	0.5794 (14)	0.3348 (6)	0.267 (5)	0.330 (3)
H14D	−0.0472	0.5964	0.2773	0.401*	0.330 (3)
H14E	−0.0120	0.5683	0.3942	0.401*	0.330 (3)
H14F	0.0910	0.4623	0.3268	0.401*	0.330 (3)
C15'	0.2441 (9)	0.7500	0.2731 (5)	0.156 (6)	0.330 (3)
H15C	0.1831	0.7500	0.2067	0.233*	0.330 (3)
H15D	0.3084	0.8651	0.2821	0.233*	0.330 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0670 (9)	0.1361 (15)	0.0685 (9)	0.000	0.0138 (8)	0.000
N1	0.0763 (13)	0.1281 (19)	0.1307 (17)	0.000	0.0140 (13)	0.000
N2	0.1355 (18)	0.0949 (16)	0.0873 (13)	0.000	−0.0027 (14)	0.000
C1	0.0721 (13)	0.0725 (15)	0.0832 (15)	0.000	0.0122 (12)	0.000
C2	0.1040 (17)	0.0628 (15)	0.0774 (14)	0.000	0.0101 (14)	0.000
C3	0.0640 (12)	0.0581 (13)	0.0697 (12)	0.000	0.0098 (10)	0.000
C4	0.0782 (14)	0.0559 (13)	0.0712 (13)	0.000	0.0107 (12)	0.000
C5	0.0889 (15)	0.0795 (16)	0.0784 (14)	0.000	0.0270 (13)	0.000
C6	0.0656 (13)	0.1008 (19)	0.0908 (15)	0.000	0.0209 (12)	0.000
C7	0.0666 (13)	0.0927 (18)	0.0756 (14)	0.000	0.0114 (12)	0.000
C8	0.0643 (12)	0.0712 (15)	0.0716 (13)	0.000	0.0163 (11)	0.000
C9	0.0673 (13)	0.0968 (18)	0.0642 (13)	0.000	0.0088 (11)	0.000
C10	0.1262 (15)	0.0906 (14)	0.0909 (11)	−0.0001 (13)	−0.0039 (11)	0.0105 (11)
C11	0.1277 (15)	0.0886 (13)	0.0912 (11)	−0.0060 (13)	−0.0044 (11)	−0.0075 (11)
C12	0.0676 (13)	0.0921 (17)	0.0728 (14)	0.000	0.0173 (12)	0.000
C13	0.0802 (15)	0.118 (2)	0.0718 (14)	0.000	0.0104 (13)	0.000
C14	0.262 (5)	0.179 (4)	0.107 (2)	0.061 (4)	−0.030 (3)	−0.059 (2)
C15	0.064 (3)	0.433 (12)	0.133 (4)	0.000	0.015 (3)	0.000
C14'	0.278 (8)	0.323 (11)	0.144 (6)	−0.208 (7)	−0.118 (6)	0.073 (6)
C15'	0.111 (7)	0.309 (17)	0.048 (4)	0.000	0.018 (5)	0.000

Geometric parameters (Å, º)

O1—C8	1.355 (2)	C11—H11A	0.9300
O1—C9	1.401 (2)	C12—C11^i	1.364 (2)
N1—C1	1.139 (3)	C12—C13	1.519 (3)
N2—C2	1.139 (3)	C13—C15'	1.449 (8)
C1—C3	1.423 (3)	C13—C14'	1.474 (8)
C2—C4	1.431 (3)	C13—C14'^i	1.474 (8)
C3—C8	1.383 (3)	C13—C15	1.477 (5)
C3—C4	1.397 (3)	C13—C14	1.508 (4)
C4—C5	1.379 (3)	C13—C14^i	1.508 (4)
C5—C6	1.381 (3)	C14—H14A	0.9600
C5—H5A	0.9300	C14—H14B	0.9600
C6—C7	1.370 (3)	C14—H14C	0.9600
C6—H6A	0.9300	C15—H15A	0.9601
C7—C8	1.384 (3)	C15—H15B	0.9599
C7—H7A	0.9300	C14'—H14D	0.9600
C9—C10	1.338 (2)	C14'—H14E	0.9600
C9—C10^i	1.338 (2)	C14'—H14F	0.9600
C10—C11	1.391 (2)	C15'—H15C	0.9599
C10—H10A	0.9300	C15'—H15D	0.9600
C11—C12	1.364 (2)
C8—O1—C9	118.10 (16)	C14'—C13—C14'^i	104.1 (7)
N1—C1—C3	178.8 (3)	C15'—C13—C15	144.2 (4)
N2—C2—C4	177.4 (3)	C14'—C13—C15	53.2 (4)
C8—C3—C4	119.46 (19)	C14'^i—C13—C15	53.2 (4)
C8—C3—C1	120.2 (2)	C15'—C13—C14	56.4 (2)
C4—C3—C1	120.33 (18)	C14'—C13—C14	58.8 (4)
C5—C4—C3	120.08 (19)	C14'^i—C13—C14	137.3 (3)
C5—C4—C2	119.1 (2)	C15—C13—C14	107.7 (2)
C3—C4—C2	120.9 (2)	C15'—C13—C14^i	56.4 (2)
C4—C5—C6	119.5 (2)	C14'—C13—C14^i	137.3 (3)
C4—C5—H5A	120.2	C14'^i—C13—C14^i	58.8 (4)
C6—C5—H5A	120.2	C15—C13—C14^i	107.7 (2)
C7—C6—C5	121.0 (2)	C14—C13—C14^i	105.2 (3)
C7—C6—H6A	119.5	C15'—C13—C12	106.6 (3)
C5—C6—H6A	119.5	C14'—C13—C12	109.3 (3)
C6—C7—C8	119.8 (2)	C14'^i—C13—C12	109.3 (3)
C6—C7—H7A	120.1	C15—C13—C12	109.2 (3)
C8—C7—H7A	120.1	C14—C13—C12	113.37 (17)
O1—C8—C3	115.64 (18)	C14^i—C13—C12	113.37 (17)
O1—C8—C7	124.19 (18)	C13—C14—H14A	109.5
C3—C8—C7	120.2 (2)	C13—C14—H14B	109.5
C10—C9—C10^i	120.1 (2)	C13—C14—H14C	109.5
C10—C9—O1	119.94 (10)	C13—C15—H15A	108.6
C10^i—C9—O1	119.94 (10)	C13—C15—H15B	111.2
C9—C10—C11	119.59 (18)	H15A—C15—H15B	112.0
C9—C10—H10A	120.2	C13—C14'—H14D	109.5
C11—C10—H10A	120.2	C13—C14'—H14E	109.5
C12—C11—C10	122.82 (18)	H14D—C14'—H14E	109.5
C12—C11—H11A	118.6	C13—C14'—H14F	109.5
C10—C11—H11A	118.6	H14D—C14'—H14F	109.5
C11^i—C12—C11	115.1 (2)	H14E—C14'—H14F	109.5
C11^i—C12—C13	122.44 (10)	C13—C15'—H15C	108.0
C11—C12—C13	122.44 (10)	C13—C15'—H15D	110.2
C15'—C13—C14'	113.8 (4)	H15C—C15'—H15D	109.5
C15'—C13—C14'^i	113.8 (4)

Symmetry code: (i) x, −y+3/2, z.