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The mol­ecular conformation of the title compound, C18H16N2O, is stabilized by two intra­molecular C—H...O inter­actions. The crystal packing is characterized by C—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007094/kp6082sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007094/kp6082Isup2.hkl
Contains datablock I

CCDC reference: 605109

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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
C18H16N2OF(000) = 584
Mr = 276.33Dx = 1.176 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1280 reflections
a = 10.2462 (10) Åθ = 2.4–29.3°
b = 9.4543 (12) ŵ = 0.07 mm1
c = 16.1120 (17) ÅT = 293 K
V = 1560.8 (3) Å3Tabular, colourless
Z = 40.50 × 0.40 × 0.20 mm
Data collection top
Stoe IPDS-2
diffractometer
1280 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 29.3°, θmin = 2.4°
Detector resolution: 6.67 pixels mm-1h = 1312
rotation method scansk = 1414
8384 measured reflectionsl = 220
2428 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-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 reflectionsΔρmax = 0.14 e Å3
190 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
C171.0359 (3)0.2470 (4)0.7581 (3)0.1009 (11)
H17A1.07800.15650.76130.151*
H17B1.04320.29430.81060.151*
H17C1.07700.30310.71580.151*
O10.57850 (18)0.16089 (16)0.73102 (12)0.0713 (5)
C50.5081 (2)0.0816 (2)0.67676 (15)0.0559 (6)
C40.4007 (3)0.1404 (2)0.63266 (16)0.0612 (6)
H40.37700.23270.64570.073*
C140.8037 (2)0.1402 (2)0.79978 (15)0.0566 (6)
C90.6609 (2)0.1072 (2)0.79484 (15)0.0577 (6)
C80.3644 (3)0.0589 (3)0.55642 (15)0.0598 (6)
C60.5441 (3)0.0477 (2)0.66129 (17)0.0636 (6)
H60.61360.09090.68850.076*
C30.3292 (2)0.0731 (3)0.57277 (15)0.0563 (6)
C70.4712 (3)0.1158 (2)0.60150 (16)0.0642 (7)
H70.49450.20860.58940.077*
C20.2195 (3)0.1356 (3)0.52522 (16)0.0663 (7)
C130.8728 (3)0.0895 (3)0.86855 (17)0.0722 (7)
H130.96150.10800.87440.087*
C150.8798 (3)0.2249 (3)0.73482 (18)0.0669 (7)
C100.5929 (3)0.0318 (3)0.85377 (17)0.0673 (7)
H100.50400.01380.84930.081*
C10.2924 (3)0.1275 (3)0.49196 (19)0.0735 (7)
C120.8076 (3)0.0126 (3)0.92685 (17)0.0792 (9)
H120.85360.02320.97200.095*
C110.6673 (4)0.0153 (3)0.92055 (17)0.0778 (8)
H110.62650.06630.96260.093*
C160.8094 (3)0.3600 (3)0.7282 (2)0.0865 (9)
H16A0.81130.40760.78090.130*
H16B0.72050.34240.71250.130*
H16C0.85050.41830.68700.130*
N20.1333 (3)0.1850 (3)0.48806 (17)0.0895 (8)
N10.2363 (3)0.1798 (3)0.43933 (19)0.1064 (10)
C180.8757 (4)0.1564 (3)0.65067 (18)0.0922 (10)
H18A0.92200.06820.65250.138*
H18B0.91590.21770.61070.138*
H18C0.78660.13950.63510.138*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C170.088 (2)0.0839 (19)0.131 (3)0.0137 (17)0.007 (2)0.034 (2)
O10.0902 (12)0.0385 (8)0.0853 (12)0.0014 (8)0.0218 (10)0.0032 (8)
C50.0614 (14)0.0435 (11)0.0628 (14)0.0039 (11)0.0013 (12)0.0030 (11)
C40.0708 (16)0.0431 (11)0.0697 (15)0.0008 (11)0.0030 (13)0.0048 (12)
C140.0731 (15)0.0400 (10)0.0566 (13)0.0000 (11)0.0003 (12)0.0020 (10)
C90.0747 (16)0.0386 (10)0.0598 (13)0.0011 (11)0.0047 (12)0.0034 (10)
C80.0664 (15)0.0503 (12)0.0626 (14)0.0110 (12)0.0070 (13)0.0004 (12)
C60.0732 (16)0.0427 (11)0.0751 (16)0.0058 (12)0.0033 (14)0.0076 (11)
C30.0593 (14)0.0515 (12)0.0581 (13)0.0040 (11)0.0038 (12)0.0090 (11)
C70.0769 (17)0.0459 (11)0.0698 (16)0.0026 (13)0.0098 (14)0.0010 (12)
C20.0690 (17)0.0621 (15)0.0678 (15)0.0025 (14)0.0006 (14)0.0061 (13)
C130.0886 (18)0.0572 (14)0.0707 (16)0.0080 (14)0.0115 (15)0.0019 (13)
C150.0773 (16)0.0502 (12)0.0732 (16)0.0004 (13)0.0091 (14)0.0073 (12)
C100.0772 (18)0.0483 (13)0.0765 (18)0.0114 (12)0.0050 (14)0.0041 (13)
C10.0778 (18)0.0666 (15)0.0762 (17)0.0155 (15)0.0044 (16)0.0029 (15)
C120.121 (3)0.0555 (14)0.0614 (15)0.0157 (16)0.0184 (16)0.0055 (13)
C110.119 (3)0.0540 (14)0.0599 (16)0.0191 (15)0.0036 (16)0.0001 (13)
C160.107 (2)0.0470 (13)0.105 (2)0.0000 (15)0.0173 (19)0.0153 (16)
N20.0889 (17)0.0884 (16)0.0913 (17)0.0063 (16)0.0166 (15)0.0100 (16)
N10.121 (2)0.096 (2)0.1022 (19)0.0256 (18)0.015 (2)0.0162 (19)
C180.128 (3)0.0772 (19)0.0713 (18)0.006 (2)0.0310 (19)0.0025 (16)
Geometric parameters (Å, º) top
C17—C151.656 (4)C3—C21.484 (4)
C17—H17A0.9600C7—H70.9300
C17—H17B0.9600C2—N21.164 (3)
C17—H17C0.9600C13—C121.363 (4)
O1—C51.359 (3)C13—H130.9300
O1—C91.424 (3)C15—C161.471 (4)
C5—C61.302 (3)C15—C181.503 (4)
C5—C41.423 (4)C10—C111.392 (4)
C4—C31.368 (4)C10—H100.9300
C4—H40.9300C1—N11.137 (3)
C14—C131.399 (4)C12—C111.466 (4)
C14—C91.499 (4)C12—H120.9300
C14—C151.531 (3)C11—H110.9300
C9—C101.376 (4)C16—H16A0.9600
C8—C31.325 (3)C16—H16B0.9600
C8—C71.420 (4)C16—H16C0.9600
C8—C11.430 (4)C18—H18A0.9600
C6—C71.378 (4)C18—H18B0.9600
C6—H60.9300C18—H18C0.9600
C15—C17—H17A109.5C12—C13—C14118.7 (3)
C15—C17—H17B109.5C12—C13—H13120.6
H17A—C17—H17B109.5C14—C13—H13120.7
C15—C17—H17C109.5C16—C15—C18107.2 (3)
H17A—C17—H17C109.5C16—C15—C14104.7 (2)
H17B—C17—H17C109.5C18—C15—C14112.2 (2)
C5—O1—C9125.65 (17)C16—C15—C17112.3 (2)
C6—C5—O1119.4 (2)C18—C15—C17106.6 (3)
C6—C5—C4119.4 (2)C14—C15—C17113.8 (2)
O1—C5—C4121.1 (2)C9—C10—C11115.0 (3)
C3—C4—C5125.8 (2)C9—C10—H10122.5
C3—C4—H4117.1C11—C10—H10122.5
C5—C4—H4117.1N1—C1—C8178.3 (3)
C13—C14—C9117.7 (2)C13—C12—C11122.0 (3)
C13—C14—C15117.6 (2)C13—C12—H12119.0
C9—C14—C15124.7 (2)C11—C12—H12119.0
C10—C9—O1112.5 (2)C10—C11—C12122.2 (3)
C10—C9—C14124.4 (2)C10—C11—H11118.9
O1—C9—C14122.9 (2)C12—C11—H11118.9
C3—C8—C7117.7 (2)C15—C16—H16A109.5
C3—C8—C1115.5 (3)C15—C16—H16B109.5
C7—C8—C1126.7 (2)H16A—C16—H16B109.5
C5—C6—C7114.8 (2)C15—C16—H16C109.5
C5—C6—H6122.6H16A—C16—H16C109.5
C7—C6—H6122.6H16B—C16—H16C109.5
C8—C3—C4115.6 (2)C15—C18—H18A109.5
C8—C3—C2118.6 (2)C15—C18—H18B109.5
C4—C3—C2125.8 (2)H18A—C18—H18B109.5
C6—C7—C8126.8 (2)C15—C18—H18C109.5
C6—C7—H7116.6H18A—C18—H18C109.5
C8—C7—H7116.6H18B—C18—H18C109.5
N2—C2—C3179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16B···O10.962.273.024 (4)135
C18—H18C···O10.962.643.309 (4)127
C7—H7···N1i0.932.733.398 (4)129
Symmetry code: (i) x+1/2, y1/2, z+1.
 

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