Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the structure of the title compound, C15H8N2O3, the phthalo­nitrile group and the 3,4-methyl­ene­dioxy­phenoxy substituent are twisted with respect to one another by 58.89 (3)°. In the crystal structure, the mol­ecules are stacked in the a-axis direction and are connected via weak C—H...N intermolecular contacts into chains, which extend in the direction of the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033094/nc6012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033094/nc6012Isup2.hkl
Contains datablock I

CCDC reference: 262482

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.127
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C3 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C4 ... 1.44 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 N1 -C1 -C3 -C8 -84.00 10.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2 N1 -C1 -C3 -C4 95.00 10.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 7 N2 -C2 -C4 -C5 -15.00 8.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8 N2 -C2 -C4 -C3 165.00 7.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 1 ALERT type 3 Indicator that the structure quality may be low 4 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, 1999).

4-(3,4-Methylenedioxyphenoxy)phthalonitrile top
Crystal data top
C15H8N2O3F(000) = 544
Mr = 264.23Dx = 1.445 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 22043 reflections
a = 4.0159 (3) Åθ = 1.6–27.2°
b = 23.6948 (14) ŵ = 0.10 mm1
c = 12.7652 (11) ÅT = 293 K
β = 91.642 (7)°Prism, colourless
V = 1214.19 (16) Å30.65 × 0.48 × 0.33 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
1887 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.098
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
Detector resolution: 6.67 pixels mm-1h = 44
w scansk = 2929
13225 measured reflectionsl = 1515
2363 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)] = 0.045H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0662P)2 + 0.0684P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2363 reflectionsΔρmax = 0.13 e Å3
182 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.099 (11)
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
C10.5159 (5)0.22249 (7)0.41417 (15)0.0741 (5)
C20.1359 (4)0.30013 (6)0.28542 (13)0.0660 (4)
C30.4136 (4)0.27614 (6)0.45485 (12)0.0596 (4)
C40.2317 (4)0.31383 (6)0.39171 (11)0.0565 (4)
C50.1391 (4)0.36576 (6)0.43059 (11)0.0572 (4)
H50.01920.39090.38810.069*
C60.2249 (4)0.38033 (6)0.53269 (11)0.0551 (4)
C70.4040 (4)0.34352 (6)0.59660 (12)0.0598 (4)
H70.46050.35340.66530.072*
C80.4981 (4)0.29167 (6)0.55694 (13)0.0629 (4)
H80.61990.26690.59950.076*
C90.1880 (4)0.45605 (6)0.65956 (11)0.0583 (4)
C100.3502 (4)0.50777 (6)0.65920 (11)0.0604 (4)
H100.43170.52340.59820.072*
C110.3826 (4)0.53426 (6)0.75389 (11)0.0591 (4)
C120.2638 (4)0.51123 (6)0.84437 (11)0.0603 (4)
C130.1100 (5)0.46004 (7)0.84492 (13)0.0682 (4)
H130.03400.44430.90660.082*
C140.0710 (4)0.43213 (7)0.74927 (13)0.0663 (4)
H140.03450.39720.74620.080*
C150.4877 (5)0.59495 (7)0.88421 (13)0.0751 (5)
H15A0.70540.59950.91810.090*
H15B0.35940.62890.89580.090*
N10.6026 (6)0.18037 (7)0.38148 (17)0.1056 (6)
N20.0547 (5)0.29023 (7)0.20087 (13)0.0877 (5)
O10.1209 (3)0.43296 (4)0.56005 (8)0.0725 (4)
O20.5222 (4)0.58586 (5)0.77471 (10)0.0844 (4)
O30.3233 (4)0.54775 (5)0.92643 (9)0.0821 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0836 (12)0.0556 (9)0.0835 (12)0.0031 (8)0.0077 (9)0.0003 (8)
C20.0721 (10)0.0579 (8)0.0680 (10)0.0015 (7)0.0025 (8)0.0080 (7)
C30.0619 (9)0.0485 (7)0.0688 (9)0.0023 (6)0.0093 (7)0.0032 (6)
C40.0597 (9)0.0528 (7)0.0572 (8)0.0053 (6)0.0058 (6)0.0002 (6)
C50.0645 (9)0.0545 (8)0.0526 (8)0.0020 (6)0.0024 (6)0.0041 (6)
C60.0634 (9)0.0499 (7)0.0522 (8)0.0006 (6)0.0050 (6)0.0031 (5)
C70.0659 (9)0.0577 (8)0.0557 (8)0.0030 (6)0.0002 (6)0.0065 (6)
C80.0661 (10)0.0543 (8)0.0684 (10)0.0019 (6)0.0028 (7)0.0123 (7)
C90.0709 (10)0.0564 (8)0.0476 (8)0.0109 (6)0.0017 (6)0.0004 (6)
C100.0816 (11)0.0507 (7)0.0496 (8)0.0105 (7)0.0152 (7)0.0057 (6)
C110.0751 (10)0.0498 (7)0.0529 (8)0.0063 (6)0.0132 (7)0.0014 (6)
C120.0728 (10)0.0623 (8)0.0464 (8)0.0110 (7)0.0103 (6)0.0009 (6)
C130.0790 (11)0.0725 (9)0.0537 (9)0.0005 (8)0.0154 (7)0.0104 (7)
C140.0738 (10)0.0633 (9)0.0620 (9)0.0046 (7)0.0061 (7)0.0063 (7)
C150.0921 (12)0.0719 (10)0.0618 (10)0.0011 (8)0.0090 (8)0.0114 (8)
N10.1274 (16)0.0660 (10)0.1237 (16)0.0164 (9)0.0079 (12)0.0138 (10)
N20.1000 (12)0.0855 (10)0.0768 (11)0.0034 (8)0.0090 (8)0.0225 (8)
O10.1070 (9)0.0564 (6)0.0534 (6)0.0159 (5)0.0092 (6)0.0028 (4)
O20.1324 (12)0.0581 (6)0.0641 (7)0.0128 (6)0.0256 (7)0.0075 (5)
O30.1227 (11)0.0746 (7)0.0498 (7)0.0015 (7)0.0167 (6)0.0076 (5)
Geometric parameters (Å, º) top
C1—N11.140 (2)C9—C101.388 (2)
C1—C31.438 (2)C9—O11.4022 (17)
C2—N21.143 (2)C10—C111.365 (2)
C2—C41.437 (2)C10—H100.9300
C3—C81.387 (2)C11—O21.368 (2)
C3—C41.395 (2)C11—C121.375 (2)
C4—C51.382 (2)C12—C131.361 (2)
C5—C61.382 (2)C12—O31.3744 (19)
C5—H50.9300C13—C141.393 (2)
C6—O11.3637 (17)C13—H130.9300
C6—C71.382 (2)C14—H140.9300
C7—C81.385 (2)C15—O31.413 (2)
C7—H70.9300C15—O21.425 (2)
C8—H80.9300C15—H15A0.9700
C9—C141.373 (2)C15—H15B0.9700
N1—C1—C3178.8 (2)C11—C10—H10122.1
N2—C2—C4178.45 (19)C9—C10—H10122.1
C8—C3—C4118.87 (13)C10—C11—O2127.67 (13)
C8—C3—C1120.62 (15)C10—C11—C12122.33 (14)
C4—C3—C1120.50 (15)O2—C11—C12109.98 (13)
C5—C4—C3120.28 (14)C13—C12—O3128.77 (14)
C5—C4—C2118.21 (14)C13—C12—C11121.76 (14)
C3—C4—C2121.50 (13)O3—C12—C11109.47 (14)
C4—C5—C6119.91 (14)C12—C13—C14117.26 (14)
C4—C5—H5120.0C12—C13—H13121.4
C6—C5—H5120.0C14—C13—H13121.4
O1—C6—C7125.73 (13)C9—C14—C13120.16 (15)
O1—C6—C5113.57 (13)C9—C14—H14119.9
C7—C6—C5120.69 (14)C13—C14—H14119.9
C6—C7—C8119.13 (14)O3—C15—O2108.30 (13)
C6—C7—H7120.4O3—C15—H15A110.0
C8—C7—H7120.4O2—C15—H15A110.0
C7—C8—C3121.11 (14)O3—C15—H15B110.0
C7—C8—H8119.4O2—C15—H15B110.0
C3—C8—H8119.4H15A—C15—H15B108.4
C14—C9—C10122.64 (14)C6—O1—C9122.45 (11)
C14—C9—O1122.21 (15)C11—O2—C15105.95 (12)
C10—C9—O1114.81 (13)C12—O3—C15106.30 (12)
C11—C10—C9115.84 (13)
N1—C1—C3—C884 (10)C9—C10—C11—C120.3 (2)
N1—C1—C3—C495 (10)C10—C11—C12—C130.9 (3)
C8—C3—C4—C50.2 (2)O2—C11—C12—C13179.43 (16)
C1—C3—C4—C5178.82 (14)C10—C11—C12—O3178.37 (15)
C8—C3—C4—C2179.83 (14)O2—C11—C12—O30.2 (2)
C1—C3—C4—C21.1 (2)O3—C12—C13—C14177.82 (16)
N2—C2—C4—C515 (8)C11—C12—C13—C141.3 (3)
N2—C2—C4—C3165 (7)C10—C9—C14—C130.6 (3)
C3—C4—C5—C60.4 (2)O1—C9—C14—C13172.36 (15)
C2—C4—C5—C6179.61 (14)C12—C13—C14—C90.6 (3)
C4—C5—C6—O1179.27 (13)C7—C6—O1—C90.1 (2)
C4—C5—C6—C70.2 (2)C5—C6—O1—C9178.88 (14)
O1—C6—C7—C8178.71 (14)C14—C9—O1—C662.0 (2)
C5—C6—C7—C80.2 (2)C10—C9—O1—C6124.53 (15)
C6—C7—C8—C30.4 (2)C10—C11—O2—C15178.57 (17)
C4—C3—C8—C70.2 (2)C12—C11—O2—C150.1 (2)
C1—C3—C8—C7179.27 (15)O3—C15—O2—C110.4 (2)
C14—C9—C10—C111.0 (2)C13—C12—O3—C15179.58 (18)
O1—C9—C10—C11172.44 (14)C11—C12—O3—C150.40 (19)
C9—C10—C11—O2178.00 (16)O2—C15—O3—C120.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···N2i0.932.533.450 (2)168
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds