The molecular conformation of the title compound, C
18H
16N
2O, is stabilized by two intramolecular C—H
O interactions. The crystal packing is characterized by C—H
N hydrogen bonds.
Supporting information
CCDC reference: 605109
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.116
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT036_ALERT_1_A No s.u. Given for Flack Parameter .............. ?
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15
PLAT361_ALERT_2_C Long C(sp3)-C(sp3) Bond C15 - C17 ... 1.66 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C8 ... 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3 ... 1.48 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18C .. O1 .. 2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. N1 .. 2.73 Ang.
Alert level G
REFLT03_ALERT_4_G 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.
From the CIF: _diffrn_reflns_theta_max 29.32
From the CIF: _reflns_number_total 2428
Count of symmetry unique reflns 2429
Completeness (_total/calc) 99.96%
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
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
3 ALERT type 4 Improvement, methodology, query or suggestion
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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
4-(2-
tert-Butylphenoxy)phthalonitrile
top
Crystal data top
C18H16N2O | F(000) = 584 |
Mr = 276.33 | Dx = 1.176 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1280 reflections |
a = 10.2462 (10) Å | θ = 2.4–29.3° |
b = 9.4543 (12) Å | µ = 0.07 mm−1 |
c = 16.1120 (17) Å | T = 293 K |
V = 1560.8 (3) Å3 | Tabular, colourless |
Z = 4 | 0.50 × 0.40 × 0.20 mm |
Data collection top
Stoe IPDS-2 diffractometer | 1280 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.065 |
Graphite monochromator | θmax = 29.3°, θmin = 2.4° |
Detector resolution: 6.67 pixels mm-1 | h = −13→12 |
rotation method scans | k = −14→14 |
8384 measured reflections | l = −22→0 |
2428 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max = 0.032 |
2428 reflections | Δρmax = 0.14 e Å−3 |
190 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Absolute structure: Flack (1983), with how many Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (0) |
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 | |
C17 | 1.0359 (3) | 0.2470 (4) | 0.7581 (3) | 0.1009 (11) | |
H17A | 1.0780 | 0.1565 | 0.7613 | 0.151* | |
H17B | 1.0432 | 0.2943 | 0.8106 | 0.151* | |
H17C | 1.0770 | 0.3031 | 0.7158 | 0.151* | |
O1 | 0.57850 (18) | 0.16089 (16) | 0.73102 (12) | 0.0713 (5) | |
C5 | 0.5081 (2) | 0.0816 (2) | 0.67676 (15) | 0.0559 (6) | |
C4 | 0.4007 (3) | 0.1404 (2) | 0.63266 (16) | 0.0612 (6) | |
H4 | 0.3770 | 0.2327 | 0.6457 | 0.073* | |
C14 | 0.8037 (2) | 0.1402 (2) | 0.79978 (15) | 0.0566 (6) | |
C9 | 0.6609 (2) | 0.1072 (2) | 0.79484 (15) | 0.0577 (6) | |
C8 | 0.3644 (3) | −0.0589 (3) | 0.55642 (15) | 0.0598 (6) | |
C6 | 0.5441 (3) | −0.0477 (2) | 0.66129 (17) | 0.0636 (6) | |
H6 | 0.6136 | −0.0909 | 0.6885 | 0.076* | |
C3 | 0.3292 (2) | 0.0731 (3) | 0.57277 (15) | 0.0563 (6) | |
C7 | 0.4712 (3) | −0.1158 (2) | 0.60150 (16) | 0.0642 (7) | |
H7 | 0.4945 | −0.2086 | 0.5894 | 0.077* | |
C2 | 0.2195 (3) | 0.1356 (3) | 0.52522 (16) | 0.0663 (7) | |
C13 | 0.8728 (3) | 0.0895 (3) | 0.86855 (17) | 0.0722 (7) | |
H13 | 0.9615 | 0.1080 | 0.8744 | 0.087* | |
C15 | 0.8798 (3) | 0.2249 (3) | 0.73482 (18) | 0.0669 (7) | |
C10 | 0.5929 (3) | 0.0318 (3) | 0.85377 (17) | 0.0673 (7) | |
H10 | 0.5040 | 0.0138 | 0.8493 | 0.081* | |
C1 | 0.2924 (3) | −0.1275 (3) | 0.49196 (19) | 0.0735 (7) | |
C12 | 0.8076 (3) | 0.0126 (3) | 0.92685 (17) | 0.0792 (9) | |
H12 | 0.8536 | −0.0232 | 0.9720 | 0.095* | |
C11 | 0.6673 (4) | −0.0153 (3) | 0.92055 (17) | 0.0778 (8) | |
H11 | 0.6265 | −0.0663 | 0.9626 | 0.093* | |
C16 | 0.8094 (3) | 0.3600 (3) | 0.7282 (2) | 0.0865 (9) | |
H16A | 0.8113 | 0.4076 | 0.7809 | 0.130* | |
H16B | 0.7205 | 0.3424 | 0.7125 | 0.130* | |
H16C | 0.8505 | 0.4183 | 0.6870 | 0.130* | |
N2 | 0.1333 (3) | 0.1850 (3) | 0.48806 (17) | 0.0895 (8) | |
N1 | 0.2363 (3) | −0.1798 (3) | 0.43933 (19) | 0.1064 (10) | |
C18 | 0.8757 (4) | 0.1564 (3) | 0.65067 (18) | 0.0922 (10) | |
H18A | 0.9220 | 0.0682 | 0.6525 | 0.138* | |
H18B | 0.9159 | 0.2177 | 0.6107 | 0.138* | |
H18C | 0.7866 | 0.1395 | 0.6351 | 0.138* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C17 | 0.088 (2) | 0.0839 (19) | 0.131 (3) | −0.0137 (17) | 0.007 (2) | 0.034 (2) |
O1 | 0.0902 (12) | 0.0385 (8) | 0.0853 (12) | −0.0014 (8) | −0.0218 (10) | 0.0032 (8) |
C5 | 0.0614 (14) | 0.0435 (11) | 0.0628 (14) | −0.0039 (11) | −0.0013 (12) | 0.0030 (11) |
C4 | 0.0708 (16) | 0.0431 (11) | 0.0697 (15) | −0.0008 (11) | 0.0030 (13) | 0.0048 (12) |
C14 | 0.0731 (15) | 0.0400 (10) | 0.0566 (13) | 0.0000 (11) | −0.0003 (12) | −0.0020 (10) |
C9 | 0.0747 (16) | 0.0386 (10) | 0.0598 (13) | 0.0011 (11) | −0.0047 (12) | −0.0034 (10) |
C8 | 0.0664 (15) | 0.0503 (12) | 0.0626 (14) | −0.0110 (12) | 0.0070 (13) | 0.0004 (12) |
C6 | 0.0732 (16) | 0.0427 (11) | 0.0751 (16) | 0.0058 (12) | −0.0033 (14) | 0.0076 (11) |
C3 | 0.0593 (14) | 0.0515 (12) | 0.0581 (13) | −0.0040 (11) | 0.0038 (12) | 0.0090 (11) |
C7 | 0.0769 (17) | 0.0459 (11) | 0.0698 (16) | −0.0026 (13) | 0.0098 (14) | −0.0010 (12) |
C2 | 0.0690 (17) | 0.0621 (15) | 0.0678 (15) | −0.0025 (14) | 0.0006 (14) | 0.0061 (13) |
C13 | 0.0886 (18) | 0.0572 (14) | 0.0707 (16) | −0.0080 (14) | −0.0115 (15) | 0.0019 (13) |
C15 | 0.0773 (16) | 0.0502 (12) | 0.0732 (16) | 0.0004 (13) | 0.0091 (14) | 0.0073 (12) |
C10 | 0.0772 (18) | 0.0483 (13) | 0.0765 (18) | −0.0114 (12) | 0.0050 (14) | −0.0041 (13) |
C1 | 0.0778 (18) | 0.0666 (15) | 0.0762 (17) | −0.0155 (15) | 0.0044 (16) | −0.0029 (15) |
C12 | 0.121 (3) | 0.0555 (14) | 0.0614 (15) | −0.0157 (16) | −0.0184 (16) | 0.0055 (13) |
C11 | 0.119 (3) | 0.0540 (14) | 0.0599 (16) | −0.0191 (15) | 0.0036 (16) | 0.0001 (13) |
C16 | 0.107 (2) | 0.0470 (13) | 0.105 (2) | 0.0000 (15) | 0.0173 (19) | 0.0153 (16) |
N2 | 0.0889 (17) | 0.0884 (16) | 0.0913 (17) | 0.0063 (16) | −0.0166 (15) | 0.0100 (16) |
N1 | 0.121 (2) | 0.096 (2) | 0.1022 (19) | −0.0256 (18) | −0.015 (2) | −0.0162 (19) |
C18 | 0.128 (3) | 0.0772 (19) | 0.0713 (18) | 0.006 (2) | 0.0310 (19) | 0.0025 (16) |
Geometric parameters (Å, º) top
C17—C15 | 1.656 (4) | C3—C2 | 1.484 (4) |
C17—H17A | 0.9600 | C7—H7 | 0.9300 |
C17—H17B | 0.9600 | C2—N2 | 1.164 (3) |
C17—H17C | 0.9600 | C13—C12 | 1.363 (4) |
O1—C5 | 1.359 (3) | C13—H13 | 0.9300 |
O1—C9 | 1.424 (3) | C15—C16 | 1.471 (4) |
C5—C6 | 1.302 (3) | C15—C18 | 1.503 (4) |
C5—C4 | 1.423 (4) | C10—C11 | 1.392 (4) |
C4—C3 | 1.368 (4) | C10—H10 | 0.9300 |
C4—H4 | 0.9300 | C1—N1 | 1.137 (3) |
C14—C13 | 1.399 (4) | C12—C11 | 1.466 (4) |
C14—C9 | 1.499 (4) | C12—H12 | 0.9300 |
C14—C15 | 1.531 (3) | C11—H11 | 0.9300 |
C9—C10 | 1.376 (4) | C16—H16A | 0.9600 |
C8—C3 | 1.325 (3) | C16—H16B | 0.9600 |
C8—C7 | 1.420 (4) | C16—H16C | 0.9600 |
C8—C1 | 1.430 (4) | C18—H18A | 0.9600 |
C6—C7 | 1.378 (4) | C18—H18B | 0.9600 |
C6—H6 | 0.9300 | C18—H18C | 0.9600 |
| | | |
C15—C17—H17A | 109.5 | C12—C13—C14 | 118.7 (3) |
C15—C17—H17B | 109.5 | C12—C13—H13 | 120.6 |
H17A—C17—H17B | 109.5 | C14—C13—H13 | 120.7 |
C15—C17—H17C | 109.5 | C16—C15—C18 | 107.2 (3) |
H17A—C17—H17C | 109.5 | C16—C15—C14 | 104.7 (2) |
H17B—C17—H17C | 109.5 | C18—C15—C14 | 112.2 (2) |
C5—O1—C9 | 125.65 (17) | C16—C15—C17 | 112.3 (2) |
C6—C5—O1 | 119.4 (2) | C18—C15—C17 | 106.6 (3) |
C6—C5—C4 | 119.4 (2) | C14—C15—C17 | 113.8 (2) |
O1—C5—C4 | 121.1 (2) | C9—C10—C11 | 115.0 (3) |
C3—C4—C5 | 125.8 (2) | C9—C10—H10 | 122.5 |
C3—C4—H4 | 117.1 | C11—C10—H10 | 122.5 |
C5—C4—H4 | 117.1 | N1—C1—C8 | 178.3 (3) |
C13—C14—C9 | 117.7 (2) | C13—C12—C11 | 122.0 (3) |
C13—C14—C15 | 117.6 (2) | C13—C12—H12 | 119.0 |
C9—C14—C15 | 124.7 (2) | C11—C12—H12 | 119.0 |
C10—C9—O1 | 112.5 (2) | C10—C11—C12 | 122.2 (3) |
C10—C9—C14 | 124.4 (2) | C10—C11—H11 | 118.9 |
O1—C9—C14 | 122.9 (2) | C12—C11—H11 | 118.9 |
C3—C8—C7 | 117.7 (2) | C15—C16—H16A | 109.5 |
C3—C8—C1 | 115.5 (3) | C15—C16—H16B | 109.5 |
C7—C8—C1 | 126.7 (2) | H16A—C16—H16B | 109.5 |
C5—C6—C7 | 114.8 (2) | C15—C16—H16C | 109.5 |
C5—C6—H6 | 122.6 | H16A—C16—H16C | 109.5 |
C7—C6—H6 | 122.6 | H16B—C16—H16C | 109.5 |
C8—C3—C4 | 115.6 (2) | C15—C18—H18A | 109.5 |
C8—C3—C2 | 118.6 (2) | C15—C18—H18B | 109.5 |
C4—C3—C2 | 125.8 (2) | H18A—C18—H18B | 109.5 |
C6—C7—C8 | 126.8 (2) | C15—C18—H18C | 109.5 |
C6—C7—H7 | 116.6 | H18A—C18—H18C | 109.5 |
C8—C7—H7 | 116.6 | H18B—C18—H18C | 109.5 |
N2—C2—C3 | 179.8 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16B···O1 | 0.96 | 2.27 | 3.024 (4) | 135 |
C18—H18C···O1 | 0.96 | 2.64 | 3.309 (4) | 127 |
C7—H7···N1i | 0.93 | 2.73 | 3.398 (4) | 129 |
Symmetry code: (i) x+1/2, −y−1/2, −z+1. |