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The crystal structure of the title compound, C16H12N2O3, is composed of a 3,5-di­methoxy­phenoxy group attached to a phthalo­nitrile group. The structure is stabilized by intermol­ecular C—H...N contacts, in additional to weak van der Waals interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010311/ac6096sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010311/ac6096Isup2.hkl
Contains datablock I

CCDC reference: 242298

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.111
  • Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C7 .. 5.38 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O1 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C4 - C7 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C8 ... 1.44 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C16 H12 N2 O3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 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 2 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-RED (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); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

4-(3,5-Dimethylphenoxy)phthalonitrile top
Crystal data top
C16H12N2O3F(000) = 584
Mr = 280.28Dx = 1.322 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.8923 (12) ÅCell parameters from 9537 reflections
b = 7.4816 (5) Åθ = 1.4–28.6°
c = 16.2916 (18) ŵ = 0.09 mm1
β = 116.331 (7)°T = 293 K
V = 1408.4 (2) Å3Prism, colourless
Z = 40.50 × 0.34 × 0.25 mm
Data collection top
Stoe IPDS-2
diffractometer
2238 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
Graphite monochromatorθmax = 28.8°, θmin = 1.8°
Detector resolution: 6.67 pixels mm-1h = 1717
ω scansk = 109
17632 measured reflectionsl = 2221
3632 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)] = 0.038H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.062P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
3632 reflectionsΔρmax = 0.18 e Å3
191 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (2)
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
C10.40434 (10)0.16856 (17)0.45390 (8)0.0471 (3)
C20.49212 (10)0.17076 (19)0.36571 (9)0.0526 (3)
H20.47770.13430.31710.063*
C30.60146 (10)0.22728 (18)0.34976 (8)0.0515 (3)
H30.66040.23040.29020.062*
C40.62384 (9)0.27905 (16)0.42159 (8)0.0446 (3)
C50.53473 (9)0.27226 (15)0.51109 (7)0.0415 (3)
C60.42523 (9)0.21732 (16)0.52735 (8)0.0452 (3)
H60.36610.21300.58680.054*
C70.73690 (10)0.33912 (19)0.40694 (9)0.0553 (3)
C80.55785 (10)0.32081 (18)0.58661 (8)0.0521 (3)
C90.24749 (10)0.10729 (19)0.41552 (8)0.0504 (3)
C100.18105 (10)0.04093 (18)0.42203 (9)0.0512 (3)
H100.17560.13490.46110.061*
C110.12282 (10)0.04528 (17)0.36867 (9)0.0515 (3)
C120.13113 (10)0.09554 (18)0.31063 (9)0.0516 (3)
H120.09120.09150.27510.062*
C130.19846 (9)0.24063 (17)0.30587 (8)0.0468 (3)
C140.25831 (10)0.24898 (18)0.35916 (9)0.0527 (3)
H140.30390.34720.35650.063*
C150.03583 (15)0.3250 (2)0.43080 (12)0.0739 (4)
H15A0.01370.41300.42360.111*
H15B0.00010.27960.49230.111*
H15C0.10880.37870.41880.111*
C160.12997 (11)0.4020 (2)0.21398 (11)0.0714 (4)
H16A0.14720.50760.17680.107*
H16B0.05310.41050.26290.107*
H16C0.13520.29910.17710.107*
N10.82476 (10)0.3869 (2)0.39814 (10)0.0824 (4)
N20.57813 (12)0.3585 (2)0.64528 (9)0.0809 (4)
O10.29516 (7)0.10852 (16)0.47769 (6)0.0679 (3)
O20.05396 (10)0.18266 (14)0.36828 (8)0.0760 (3)
O30.21116 (7)0.38505 (13)0.25131 (7)0.0619 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0442 (6)0.0592 (7)0.0479 (7)0.0081 (5)0.0295 (5)0.0084 (5)
C20.0539 (7)0.0708 (8)0.0437 (6)0.0029 (6)0.0313 (5)0.0004 (6)
C30.0449 (6)0.0713 (8)0.0404 (6)0.0013 (6)0.0208 (5)0.0009 (6)
C40.0395 (5)0.0525 (7)0.0465 (6)0.0007 (5)0.0233 (5)0.0035 (5)
C50.0453 (6)0.0443 (6)0.0423 (6)0.0008 (5)0.0262 (5)0.0003 (5)
C60.0412 (6)0.0581 (7)0.0397 (6)0.0041 (5)0.0212 (5)0.0038 (5)
C70.0457 (6)0.0728 (9)0.0510 (7)0.0074 (6)0.0245 (5)0.0075 (6)
C80.0504 (6)0.0656 (8)0.0454 (7)0.0104 (6)0.0259 (5)0.0001 (6)
C90.0420 (6)0.0732 (8)0.0451 (6)0.0081 (5)0.0276 (5)0.0052 (6)
C100.0485 (6)0.0593 (7)0.0543 (7)0.0058 (5)0.0306 (5)0.0087 (6)
C110.0528 (6)0.0548 (7)0.0573 (7)0.0078 (6)0.0338 (6)0.0015 (6)
C120.0495 (6)0.0652 (8)0.0527 (7)0.0058 (6)0.0342 (6)0.0027 (6)
C130.0398 (5)0.0577 (7)0.0472 (6)0.0029 (5)0.0231 (5)0.0075 (6)
C140.0454 (6)0.0647 (8)0.0551 (7)0.0134 (6)0.0286 (5)0.0058 (6)
C150.0853 (10)0.0599 (9)0.0862 (11)0.0218 (8)0.0468 (9)0.0135 (8)
C160.0528 (7)0.0973 (12)0.0712 (9)0.0021 (7)0.0340 (7)0.0307 (9)
N10.0527 (7)0.1207 (12)0.0774 (9)0.0245 (7)0.0322 (6)0.0140 (8)
N20.0861 (9)0.1116 (11)0.0564 (7)0.0259 (8)0.0420 (7)0.0030 (7)
O10.0517 (5)0.1132 (8)0.0526 (5)0.0298 (5)0.0355 (4)0.0219 (5)
O20.0991 (8)0.0667 (6)0.0931 (8)0.0324 (5)0.0705 (7)0.0174 (6)
O30.0528 (5)0.0730 (6)0.0697 (6)0.0122 (4)0.0360 (4)0.0237 (5)
Geometric parameters (Å, º) top
C1—O11.3599 (13)C10—C111.3781 (16)
C1—C21.3795 (17)C10—H100.9300
C1—C61.3869 (16)C11—O21.3601 (15)
C2—C31.3815 (17)C11—C121.3877 (18)
C2—H20.9300C12—C131.3705 (17)
C3—C41.3792 (17)C12—H120.9300
C3—H30.9300C13—O31.3621 (15)
C4—C51.4009 (16)C13—C141.3954 (16)
C4—C71.4404 (16)C14—H140.9300
C5—C61.3785 (15)C15—O21.4196 (18)
C5—C81.4353 (16)C15—H15A0.9600
C6—H60.9300C15—H15B0.9600
C7—N11.1347 (16)C15—H15C0.9600
C8—N21.1328 (17)C16—O31.4304 (16)
C9—C141.3685 (18)C16—H16A0.9600
C9—C101.3763 (17)C16—H16B0.9600
C9—O11.3985 (13)C16—H16C0.9600
O1—C1—C2124.61 (11)O2—C11—C12115.07 (11)
O1—C1—C6114.43 (10)C10—C11—C12120.86 (11)
C2—C1—C6120.80 (10)C13—C12—C11119.70 (11)
C1—C2—C3119.79 (11)C13—C12—H12120.2
C1—C2—H2120.1C11—C12—H12120.2
C3—C2—H2120.1O3—C13—C12123.71 (11)
C4—C3—C2120.42 (11)O3—C13—C14115.53 (10)
C4—C3—H3119.8C12—C13—C14120.76 (11)
C2—C3—H3119.8C9—C14—C13117.57 (11)
C3—C4—C5119.30 (10)C9—C14—H14121.2
C3—C4—C7121.61 (11)C13—C14—H14121.2
C5—C4—C7119.09 (11)O2—C15—H15A109.5
C6—C5—C4120.53 (10)O2—C15—H15B109.5
C6—C5—C8119.67 (10)H15A—C15—H15B109.5
C4—C5—C8119.79 (10)O2—C15—H15C109.5
C5—C6—C1119.13 (10)H15A—C15—H15C109.5
C5—C6—H6120.4H15B—C15—H15C109.5
C1—C6—H6120.4O3—C16—H16A109.5
N1—C7—C4177.96 (15)O3—C16—H16B109.5
N2—C8—C5178.78 (15)H16A—C16—H16B109.5
C14—C9—C10123.41 (11)O3—C16—H16C109.5
C14—C9—O1122.28 (11)H16A—C16—H16C109.5
C10—C9—O1114.07 (11)H16B—C16—H16C109.5
C9—C10—C11117.71 (12)C1—O1—C9121.84 (9)
C9—C10—H10121.1C11—O2—C15117.62 (11)
C11—C10—H10121.1C13—O3—C16116.67 (10)
O2—C11—C10124.07 (12)
O1—C1—C2—C3177.08 (13)O2—C11—C12—C13179.97 (12)
C6—C1—C2—C32.0 (2)C10—C11—C12—C130.3 (2)
C1—C2—C3—C40.9 (2)C11—C12—C13—O3179.62 (12)
C2—C3—C4—C50.56 (19)C11—C12—C13—C140.38 (19)
C2—C3—C4—C7179.79 (13)C10—C9—C14—C130.09 (19)
C3—C4—C5—C61.07 (18)O1—C9—C14—C13174.18 (11)
C7—C4—C5—C6179.27 (12)O3—C13—C14—C9179.58 (11)
C3—C4—C5—C8178.18 (12)C12—C13—C14—C90.27 (18)
C7—C4—C5—C81.48 (18)C2—C1—O1—C925.1 (2)
C4—C5—C6—C10.07 (18)C6—C1—O1—C9159.47 (12)
C8—C5—C6—C1179.18 (12)C14—C9—O1—C144.36 (19)
O1—C1—C6—C5177.04 (11)C10—C9—O1—C1141.04 (13)
C2—C1—C6—C51.45 (19)C10—C11—O2—C153.9 (2)
C14—C9—C10—C110.0 (2)C12—C11—O2—C15175.83 (13)
O1—C9—C10—C11174.53 (11)C12—C13—O3—C1614.54 (18)
C9—C10—C11—O2179.82 (13)C14—C13—O3—C16164.74 (12)
C9—C10—C11—C120.10 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N2i0.932.513.2621 (18)138
Symmetry code: (i) x, y1/2, z+1/2.
 

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