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.
Supporting information
CCDC reference: 294135
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
top
Crystal data top
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) Å3 | Prism, colorless |
Z = 2 | 0.4 × 0.3 × 0.1 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.001P)2 + 0.3P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
O1—C8 | 1.355 (2) | C11—H11A | 0.9300 |
O1—C9 | 1.401 (2) | C12—C11i | 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—C14i | 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—C10i | 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—C14i | 56.4 (2) |
C4—C5—C6 | 119.5 (2) | C14'—C13—C14i | 137.3 (3) |
C4—C5—H5A | 120.2 | C14'i—C13—C14i | 58.8 (4) |
C6—C5—H5A | 120.2 | C15—C13—C14i | 107.7 (2) |
C7—C6—C5 | 121.0 (2) | C14—C13—C14i | 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) | C14i—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—C10i | 120.1 (2) | C13—C14—H14C | 109.5 |
C10—C9—O1 | 119.94 (10) | C13—C15—H15A | 108.6 |
C10i—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 |
C11i—C12—C11 | 115.1 (2) | H14E—C14'—H14F | 109.5 |
C11i—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. |