The crystal structure of the title phthalonitrile derivative, C
15H
8N
2O
2, is stabilized by intermolecular C—H
O contacts.
Supporting information
CCDC reference: 298430
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.110
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT728_ALERT_1_A D-H..A Calc 164.00, Rep 1634.00 Dev... 1470.00 Deg.
C11 -H11 -O2 1.555 1.555 6.565
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
PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C4 .. 5.50 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 .. 5.96 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1
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 ... 1.43 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1
N1 -C1 -C3 -C8 -24.00 9.00 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 156.00 9.00 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 12.00 0.00 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 6.00 0.00 1.555 1.555 1.555 1.555
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
4 ALERT type 4 Improvement, methodology, query or suggestion
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),
ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
4-(2-formylphenoxy)phtalonitrile
top
Crystal data top
C15H8N2O2 | F(000) = 1024 |
Mr = 248.23 | Dx = 1.322 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 13844 reflections |
a = 23.0524 (16) Å | θ = 2.1–28.0° |
b = 8.1639 (8) Å | µ = 0.09 mm−1 |
c = 15.3994 (11) Å | T = 293 K |
β = 120.621 (5)° | Prism, colourless |
V = 2494.0 (4) Å3 | 0.42 × 0.34 × 0.23 mm |
Z = 8 | |
Data collection top
Stoe IPDS-2 diffractometer | 2982 independent reflections |
Radiation source: fine-focus sealed tube | 1934 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.9°, θmin = 2.1° |
ω scans | h = −30→28 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −10→10 |
Tmin = 0.970, Tmax = 0.982 | l = −20→20 |
16362 measured 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)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.061P)2 + 0.0525P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2982 reflections | Δρmax = 0.14 e Å−3 |
173 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0113 (15) |
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 | |
C1 | 0.01658 (6) | 0.31022 (16) | −0.10146 (10) | 0.0690 (3) | |
C2 | −0.07594 (7) | 0.56744 (17) | −0.20877 (10) | 0.0747 (4) | |
C3 | 0.03741 (6) | 0.47818 (14) | −0.07924 (8) | 0.0575 (3) | |
C4 | −0.00801 (6) | 0.60500 (15) | −0.13240 (8) | 0.0622 (3) | |
C5 | 0.01392 (6) | 0.76546 (16) | −0.10918 (10) | 0.0735 (4) | |
H5 | −0.0159 | 0.8506 | −0.1436 | 0.088* | |
C6 | 0.07922 (6) | 0.80048 (16) | −0.03588 (10) | 0.0725 (4) | |
H6 | 0.0934 | 0.9087 | −0.0203 | 0.087* | |
C7 | 0.12365 (6) | 0.67413 (15) | 0.01453 (8) | 0.0625 (3) | |
C8 | 0.10288 (6) | 0.51278 (14) | −0.00556 (8) | 0.0606 (3) | |
H8 | 0.1327 | 0.4285 | 0.0302 | 0.073* | |
C9 | 0.24048 (6) | 0.61137 (14) | 0.11144 (9) | 0.0603 (3) | |
C10 | 0.24769 (7) | 0.53638 (18) | 0.03736 (9) | 0.0738 (4) | |
H10 | 0.2159 | 0.5526 | −0.0304 | 0.089* | |
C11 | 0.30268 (8) | 0.4371 (2) | 0.06527 (12) | 0.0848 (4) | |
H11 | 0.3074 | 0.3838 | 0.0158 | 0.102* | |
C12 | 0.35080 (7) | 0.4156 (2) | 0.16518 (12) | 0.0830 (4) | |
H12 | 0.3878 | 0.3484 | 0.1831 | 0.100* | |
C13 | 0.34403 (6) | 0.49309 (17) | 0.23777 (9) | 0.0683 (3) | |
H13 | 0.3770 | 0.4795 | 0.3053 | 0.082* | |
C14 | 0.28865 (5) | 0.59215 (14) | 0.21253 (8) | 0.0571 (3) | |
C15 | 0.28313 (7) | 0.67346 (17) | 0.29301 (10) | 0.0748 (4) | |
H15 | 0.2429 | 0.7259 | 0.2759 | 0.090* | |
N1 | 0.00118 (6) | 0.17691 (16) | −0.11841 (11) | 0.1005 (5) | |
N2 | −0.13009 (7) | 0.53687 (19) | −0.26904 (11) | 0.1054 (5) | |
O1 | 0.18745 (4) | 0.71778 (11) | 0.08785 (7) | 0.0772 (3) | |
O2 | 0.32774 (6) | 0.67607 (14) | 0.37985 (7) | 0.0919 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0536 (6) | 0.0597 (8) | 0.0780 (7) | −0.0008 (5) | 0.0220 (6) | 0.0010 (6) |
C2 | 0.0601 (7) | 0.0704 (8) | 0.0710 (7) | 0.0101 (6) | 0.0170 (6) | −0.0016 (6) |
C3 | 0.0527 (6) | 0.0545 (6) | 0.0585 (6) | 0.0017 (5) | 0.0234 (5) | 0.0029 (5) |
C4 | 0.0525 (6) | 0.0629 (7) | 0.0592 (6) | 0.0065 (5) | 0.0197 (5) | 0.0025 (5) |
C5 | 0.0628 (7) | 0.0569 (7) | 0.0774 (7) | 0.0129 (5) | 0.0187 (6) | 0.0077 (6) |
C6 | 0.0652 (7) | 0.0515 (7) | 0.0800 (8) | 0.0033 (5) | 0.0218 (6) | 0.0032 (6) |
C7 | 0.0533 (6) | 0.0558 (6) | 0.0610 (6) | 0.0013 (5) | 0.0165 (5) | 0.0013 (5) |
C8 | 0.0530 (6) | 0.0529 (6) | 0.0614 (6) | 0.0050 (5) | 0.0186 (5) | 0.0081 (5) |
C9 | 0.0496 (6) | 0.0540 (6) | 0.0639 (7) | −0.0063 (5) | 0.0190 (5) | −0.0015 (5) |
C10 | 0.0670 (8) | 0.0856 (9) | 0.0583 (6) | −0.0124 (7) | 0.0245 (6) | −0.0048 (6) |
C11 | 0.0739 (9) | 0.1048 (11) | 0.0838 (9) | −0.0109 (8) | 0.0461 (8) | −0.0217 (8) |
C12 | 0.0585 (7) | 0.0931 (10) | 0.0948 (10) | 0.0046 (7) | 0.0372 (7) | −0.0093 (8) |
C13 | 0.0501 (6) | 0.0730 (8) | 0.0675 (7) | −0.0029 (5) | 0.0196 (5) | −0.0005 (6) |
C14 | 0.0501 (6) | 0.0527 (6) | 0.0591 (6) | −0.0088 (4) | 0.0210 (5) | −0.0048 (5) |
C15 | 0.0741 (8) | 0.0687 (8) | 0.0734 (8) | −0.0046 (6) | 0.0316 (7) | −0.0110 (6) |
N1 | 0.0752 (8) | 0.0640 (7) | 0.1263 (11) | −0.0082 (6) | 0.0251 (7) | −0.0049 (7) |
N2 | 0.0664 (8) | 0.1001 (10) | 0.0985 (9) | 0.0062 (7) | 0.0048 (7) | −0.0110 (7) |
O1 | 0.0564 (5) | 0.0578 (5) | 0.0815 (5) | 0.0022 (4) | 0.0090 (4) | −0.0072 (4) |
O2 | 0.1026 (7) | 0.0945 (7) | 0.0629 (5) | −0.0162 (6) | 0.0308 (5) | −0.0150 (5) |
Geometric parameters (Å, º) top
C1—N1 | 1.1333 (17) | C9—C10 | 1.3774 (18) |
C1—C3 | 1.4354 (17) | C9—C14 | 1.3857 (16) |
C2—N2 | 1.1409 (17) | C9—O1 | 1.3887 (14) |
C2—C4 | 1.4329 (17) | C10—C11 | 1.376 (2) |
C3—C8 | 1.3785 (15) | C10—H10 | 0.9300 |
C3—C4 | 1.4019 (16) | C11—C12 | 1.375 (2) |
C4—C5 | 1.3840 (18) | C11—H11 | 0.9300 |
C5—C6 | 1.3751 (18) | C12—C13 | 1.361 (2) |
C5—H5 | 0.9300 | C12—H12 | 0.9300 |
C6—C7 | 1.3804 (17) | C13—C14 | 1.3889 (17) |
C6—H6 | 0.9300 | C13—H13 | 0.9300 |
C7—O1 | 1.3687 (14) | C14—C15 | 1.4676 (18) |
C7—C8 | 1.3818 (17) | C15—O2 | 1.2023 (15) |
C8—H8 | 0.9300 | C15—H15 | 0.9300 |
| | | |
N1—C1—C3 | 178.90 (14) | C10—C9—O1 | 121.53 (11) |
N2—C2—C4 | 179.47 (18) | C14—C9—O1 | 117.37 (11) |
C8—C3—C4 | 120.54 (11) | C11—C10—C9 | 118.93 (12) |
C8—C3—C1 | 119.01 (10) | C11—C10—H10 | 120.5 |
C4—C3—C1 | 120.44 (10) | C9—C10—H10 | 120.5 |
C5—C4—C3 | 118.84 (10) | C12—C11—C10 | 120.99 (13) |
C5—C4—C2 | 121.15 (11) | C12—C11—H11 | 119.5 |
C3—C4—C2 | 120.01 (11) | C10—C11—H11 | 119.5 |
C6—C5—C4 | 120.79 (11) | C13—C12—C11 | 119.67 (14) |
C6—C5—H5 | 119.6 | C13—C12—H12 | 120.2 |
C4—C5—H5 | 119.6 | C11—C12—H12 | 120.2 |
C5—C6—C7 | 119.65 (12) | C12—C13—C14 | 120.95 (12) |
C5—C6—H6 | 120.2 | C12—C13—H13 | 119.5 |
C7—C6—H6 | 120.2 | C14—C13—H13 | 119.5 |
O1—C7—C6 | 116.55 (11) | C9—C14—C13 | 118.48 (11) |
O1—C7—C8 | 122.49 (10) | C9—C14—C15 | 122.20 (11) |
C6—C7—C8 | 120.88 (11) | C13—C14—C15 | 119.32 (11) |
C3—C8—C7 | 119.27 (10) | O2—C15—C14 | 123.66 (13) |
C3—C8—H8 | 120.4 | O2—C15—H15 | 118.2 |
C7—C8—H8 | 120.4 | C14—C15—H15 | 118.2 |
C10—C9—C14 | 120.95 (12) | C7—O1—C9 | 119.07 (9) |
| | | |
N1—C1—C3—C8 | −24 (9) | C14—C9—C10—C11 | 2.1 (2) |
N1—C1—C3—C4 | 156 (9) | O1—C9—C10—C11 | 177.49 (12) |
C8—C3—C4—C5 | −0.39 (18) | C9—C10—C11—C12 | −1.6 (2) |
C1—C3—C4—C5 | −179.77 (12) | C10—C11—C12—C13 | 0.2 (2) |
C8—C3—C4—C2 | −179.95 (11) | C11—C12—C13—C14 | 0.9 (2) |
C1—C3—C4—C2 | 0.67 (18) | C10—C9—C14—C13 | −1.06 (18) |
N2—C2—C4—C5 | −123 (21) | O1—C9—C14—C13 | −176.68 (10) |
N2—C2—C4—C3 | 57 (21) | C10—C9—C14—C15 | 178.58 (12) |
C3—C4—C5—C6 | 0.5 (2) | O1—C9—C14—C15 | 2.96 (16) |
C2—C4—C5—C6 | −179.91 (13) | C12—C13—C14—C9 | −0.42 (19) |
C4—C5—C6—C7 | 0.6 (2) | C12—C13—C14—C15 | 179.93 (13) |
C5—C6—C7—O1 | −178.79 (12) | C9—C14—C15—O2 | −170.30 (13) |
C5—C6—C7—C8 | −1.9 (2) | C13—C14—C15—O2 | 9.3 (2) |
C4—C3—C8—C7 | −0.89 (18) | C6—C7—O1—C9 | −153.46 (12) |
C1—C3—C8—C7 | 178.50 (12) | C8—C7—O1—C9 | 29.73 (18) |
O1—C7—C8—C3 | 178.73 (11) | C10—C9—O1—C7 | 45.67 (16) |
C6—C7—C8—C3 | 2.06 (19) | C14—C9—O1—C7 | −138.74 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O2i | 0.93 | 2.39 | 3.2722 (15) | 159 |
C11—H11···O2ii | 0.93 | 2.42 | 3.3199 (17) | 1634 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, −y+1, z−1/2. |