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The mol­ecule of the title compound, C17H12N2O3, is not planar. The dihedral angle between the phthalonitrile unit and methoxy­acetophenone group is 81.1 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020204/dn2041sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020204/dn2041Isup2.hkl
Contains datablock I

CCDC reference: 613661

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.074
  • wR factor = 0.143
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.181 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.18 PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C12 - C16 ... 1.53 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C3 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C4 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 5 ALERT type 3 Indicator that the structure quality may be low 0 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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-(4-Acetyl-2-methoxyphenoxy)benzene-1,2-dinitrile top
Crystal data top
C17H12N2O3F(000) = 1216
Mr = 292.29Dx = 1.301 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 11205 reflections
a = 8.3942 (7) Åθ = 1.8–27.4°
b = 22.426 (2) ŵ = 0.09 mm1
c = 15.855 (2) ÅT = 293 K
V = 2984.6 (5) Å3Prism, colourless
Z = 80.64 × 0.33 × 0.02 mm
Data collection top
Stoe IPDS II
diffractometer
3260 independent reflections
Radiation source: fine-focus sealed tube1152 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.181
Detector resolution: 6.67 pixels mm-1θmax = 27.0°, θmin = 1.8°
φ scansh = 1010
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2827
Tmin = 0.971, Tmax = 0.998l = 2020
17381 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0354P)2]
where P = (Fo2 + 2Fc2)/3
3260 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.14 e Å3
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
C40.1483 (5)0.50281 (17)0.1250 (2)0.0544 (10)
O10.1193 (3)0.38448 (12)0.19682 (19)0.0728 (9)
C120.1553 (5)0.24147 (17)0.2787 (3)0.0579 (11)
C60.0592 (4)0.43634 (17)0.1642 (3)0.0539 (10)
C160.2424 (5)0.1874 (2)0.3145 (3)0.0675 (12)
C90.0152 (4)0.33839 (18)0.2220 (3)0.0584 (11)
C50.1016 (4)0.44875 (17)0.1597 (3)0.0562 (11)
H50.17660.42160.17950.067*
C130.1343 (5)0.24997 (19)0.1934 (3)0.0701 (12)
H130.17830.22330.15500.084*
O20.0564 (4)0.37389 (13)0.3586 (2)0.0832 (9)
C20.3155 (6)0.51741 (19)0.1198 (3)0.0724 (13)
C70.1719 (5)0.47659 (19)0.1358 (3)0.0627 (11)
H70.27970.46750.13970.075*
C80.1246 (5)0.5301 (2)0.1018 (3)0.0638 (12)
H80.20100.55700.08290.077*
O30.2541 (5)0.18088 (15)0.3902 (2)0.1023 (12)
C30.0368 (5)0.54463 (17)0.0952 (3)0.0572 (11)
C10.0862 (6)0.5999 (2)0.0580 (3)0.0707 (13)
C110.0930 (4)0.28191 (17)0.3359 (3)0.0599 (11)
H110.10840.27600.39340.072*
N20.4481 (5)0.52921 (17)0.1165 (3)0.1011 (16)
C100.0073 (4)0.33154 (17)0.3078 (3)0.0575 (11)
N10.1280 (6)0.64428 (19)0.0293 (3)0.0973 (14)
C140.0457 (5)0.29921 (19)0.1649 (3)0.0718 (13)
H140.02890.30500.10750.086*
C170.3082 (6)0.14334 (18)0.2550 (3)0.0889 (16)
H17A0.37950.16290.21660.133*
H17B0.22280.12520.22390.133*
H17C0.36490.11320.28570.133*
C150.0489 (8)0.3646 (3)0.4476 (3)0.124 (2)
H15A0.10370.32830.46170.187*
H15B0.09840.39750.47610.187*
H15C0.06050.36160.46480.187*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C40.046 (2)0.050 (2)0.067 (3)0.0064 (19)0.004 (2)0.000 (2)
O10.0455 (16)0.0671 (19)0.106 (2)0.0053 (15)0.0022 (17)0.0257 (17)
C120.052 (2)0.051 (2)0.071 (3)0.002 (2)0.003 (2)0.003 (2)
C60.045 (2)0.056 (2)0.061 (3)0.008 (2)0.000 (2)0.008 (2)
C160.065 (3)0.057 (3)0.081 (3)0.003 (2)0.000 (3)0.007 (3)
C90.046 (2)0.055 (3)0.074 (3)0.002 (2)0.004 (2)0.018 (2)
C50.047 (2)0.053 (2)0.068 (3)0.0086 (19)0.006 (2)0.005 (2)
C130.073 (3)0.062 (3)0.076 (3)0.001 (2)0.009 (3)0.005 (2)
O20.085 (2)0.079 (2)0.086 (2)0.0229 (18)0.001 (2)0.0094 (19)
C20.057 (3)0.053 (3)0.107 (4)0.005 (2)0.006 (3)0.014 (3)
C70.043 (2)0.073 (3)0.072 (3)0.014 (2)0.005 (2)0.006 (2)
C80.057 (3)0.076 (3)0.059 (3)0.017 (2)0.009 (2)0.006 (2)
O30.128 (3)0.084 (2)0.095 (3)0.023 (2)0.012 (3)0.015 (2)
C30.062 (3)0.047 (2)0.063 (3)0.010 (2)0.000 (2)0.000 (2)
C10.077 (3)0.061 (3)0.074 (3)0.010 (3)0.009 (3)0.003 (3)
C110.059 (3)0.056 (2)0.064 (3)0.007 (2)0.001 (2)0.009 (2)
N20.061 (2)0.076 (3)0.166 (5)0.001 (2)0.001 (3)0.021 (3)
C100.050 (2)0.043 (2)0.080 (3)0.0018 (19)0.001 (2)0.006 (2)
N10.116 (4)0.073 (3)0.103 (3)0.003 (3)0.008 (3)0.024 (2)
C140.069 (3)0.068 (3)0.079 (3)0.008 (2)0.003 (3)0.001 (3)
C170.086 (4)0.062 (3)0.119 (4)0.014 (2)0.005 (3)0.001 (3)
C150.154 (6)0.142 (5)0.077 (4)0.048 (5)0.000 (4)0.020 (3)
Geometric parameters (Å, º) top
C4—C51.388 (5)O2—C151.427 (5)
C4—C31.407 (5)C2—N21.145 (5)
C4—C21.444 (6)C7—C81.375 (5)
O1—C61.369 (4)C7—H70.9300
O1—C91.411 (4)C8—C31.397 (5)
C12—C131.377 (5)C8—H80.9300
C12—C111.385 (5)C3—C11.433 (6)
C12—C161.525 (6)C1—N11.150 (5)
C6—C51.380 (5)C11—C101.399 (5)
C6—C71.383 (5)C11—H110.9300
C16—O31.213 (5)C14—H140.9300
C16—C171.473 (6)C17—H17A0.9600
C9—C141.361 (5)C17—H17B0.9600
C9—C101.382 (5)C17—H17C0.9600
C5—H50.9300C15—H15A0.9600
C13—C141.406 (6)C15—H15B0.9600
C13—H130.9300C15—H15C0.9600
O2—C101.355 (4)
C5—C4—C3121.8 (4)C7—C8—H8119.6
C5—C4—C2119.7 (4)C3—C8—H8119.6
C3—C4—C2118.5 (4)C8—C3—C4117.7 (4)
C6—O1—C9120.1 (3)C8—C3—C1120.8 (4)
C13—C12—C11120.3 (4)C4—C3—C1121.4 (4)
C13—C12—C16122.5 (4)N1—C1—C3178.8 (5)
C11—C12—C16117.2 (4)C12—C11—C10120.4 (4)
O1—C6—C5123.4 (3)C12—C11—H11119.8
O1—C6—C7115.2 (3)C10—C11—H11119.8
C5—C6—C7121.4 (4)O2—C10—C9117.0 (4)
O3—C16—C17121.4 (5)O2—C10—C11124.8 (4)
O3—C16—C12120.2 (5)C9—C10—C11118.2 (4)
C17—C16—C12118.4 (4)C9—C14—C13119.5 (4)
C14—C9—C10122.1 (4)C9—C14—H14120.3
C14—C9—O1121.2 (4)C13—C14—H14120.3
C10—C9—O1116.4 (4)C16—C17—H17A109.5
C6—C5—C4118.2 (4)C16—C17—H17B109.5
C6—C5—H5120.9H17A—C17—H17B109.5
C4—C5—H5120.9C16—C17—H17C109.5
C12—C13—C14119.5 (4)H17A—C17—H17C109.5
C12—C13—H13120.3H17B—C17—H17C109.5
C14—C13—H13120.3O2—C15—H15A109.5
C10—O2—C15117.9 (4)O2—C15—H15B109.5
N2—C2—C4179.3 (6)H15A—C15—H15B109.5
C8—C7—C6120.0 (4)O2—C15—H15C109.5
C8—C7—H7120.0H15A—C15—H15C109.5
C6—C7—H7120.0H15B—C15—H15C109.5
C7—C8—C3120.9 (4)
 

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