The title compound, C10H8N2O2, consisting of a benzene ring with two O—CH2—CN ortho substituents, has approximately C2 symmetry. The supramolecular structure of the compound is determined by two hydrogen bonds and two π–π stacking interactions.
Supporting information
CCDC reference: 242314
Key indicators
- Single-crystal X-ray study
- T = 293 K
- R factor = 0.048
- wR factor = 0.107
- Data-to-parameter ratio = 20.4
checkCIF/PLATON results
No syntax errors found
Alert level A
CELLV02_ALERT_1_A The supplied cell volume s.u. differs from that
calculated from the cell parameter s.u.'s by > 8
Calculated cell volume su = 36.81
Cell volume su given = 1.00
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc.
Alert level C
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 0.729
PLAT128_ALERT_4_C Non-standard setting of Space group Pbca .... Pcab
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C6 .. 6.01 su
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C12
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C62
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 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
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
2-[2-(cyanomethoxy)phenoxy]acetonitrile
top
Crystal data top
C10H8N2O2 | F(000) = 784 |
Mr = 188.18 | Dx = 1.305 Mg m−3 |
Orthorhombic, Pcab | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2bc 2ac | Cell parameters from 17120 reflections |
a = 7.4940 (12) Å | θ = 2–26° |
b = 13.9150 (11) Å | µ = 0.09 mm−1 |
c = 18.3770 (13) Å | T = 293 K |
V = 1916.34 (1) Å3 | Prism, colourless |
Z = 8 | 0.35 × 0.30 × 0.20 mm |
Data collection top
Stoe IPDS 2 diffractometer | 1014 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.100 |
Plane graphite monochromator | θmax = 29.3°, θmin = 2.2° |
Detector resolution: 6.67 pixels mm-1 | h = −9→10 |
ω scans | k = −19→19 |
17120 measured reflections | l = −25→25 |
2592 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: Full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 0.73 | w = 1/[σ2(Fo2) + (0.049P)2] where P = (Fo2 + 2Fc2)/3 |
2592 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.56101 (15) | 0.12097 (8) | 0.13824 (5) | 0.0630 (4) | |
O2 | 0.44779 (14) | 0.10632 (7) | 0.00955 (5) | 0.0560 (4) | |
N1 | 0.3478 (3) | 0.12944 (18) | 0.29636 (11) | 0.1291 (9) | |
N2 | 0.6475 (3) | 0.11757 (17) | −0.15303 (11) | 0.1286 (10) | |
C1 | 0.52487 (19) | 0.20773 (11) | 0.10516 (7) | 0.0500 (5) | |
C2 | 0.5452 (2) | 0.29701 (13) | 0.13575 (9) | 0.0657 (6) | |
C3 | 0.5065 (2) | 0.37770 (14) | 0.09472 (11) | 0.0753 (7) | |
C4 | 0.4480 (2) | 0.36928 (13) | 0.02466 (10) | 0.0726 (7) | |
C5 | 0.4276 (2) | 0.27979 (12) | −0.00639 (8) | 0.0583 (6) | |
C6 | 0.46460 (19) | 0.19941 (11) | 0.03366 (7) | 0.0465 (5) | |
C11 | 0.6193 (2) | 0.12091 (14) | 0.21123 (7) | 0.0657 (6) | |
C12 | 0.4671 (3) | 0.12699 (14) | 0.26011 (9) | 0.0735 (7) | |
C61 | 0.3889 (2) | 0.09143 (12) | −0.06267 (7) | 0.0562 (5) | |
C62 | 0.5339 (3) | 0.10733 (14) | −0.11421 (9) | 0.0748 (7) | |
H2 | 0.58452 | 0.30320 | 0.18351 | 0.0788* | |
H3 | 0.52049 | 0.43841 | 0.11510 | 0.0904* | |
H4 | 0.42174 | 0.42412 | −0.00221 | 0.0871* | |
H5 | 0.38900 | 0.27412 | −0.05429 | 0.0700* | |
H11A | 0.69808 | 0.17514 | 0.21945 | 0.0789* | |
H11B | 0.68564 | 0.06247 | 0.22104 | 0.0789* | |
H61A | 0.29149 | 0.13512 | −0.07339 | 0.0675* | |
H61B | 0.34474 | 0.02624 | −0.06774 | 0.0675* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0799 (8) | 0.0772 (8) | 0.0320 (5) | 0.0084 (6) | −0.0059 (5) | 0.0004 (5) |
O2 | 0.0753 (8) | 0.0610 (7) | 0.0318 (5) | 0.0026 (5) | −0.0067 (5) | 0.0003 (4) |
N1 | 0.1189 (16) | 0.188 (2) | 0.0804 (12) | 0.0047 (15) | 0.0451 (12) | 0.0178 (12) |
N2 | 0.1323 (18) | 0.173 (2) | 0.0804 (12) | −0.0387 (15) | 0.0520 (13) | −0.0234 (12) |
C1 | 0.0468 (9) | 0.0635 (10) | 0.0397 (7) | −0.0002 (8) | 0.0061 (6) | −0.0019 (7) |
C2 | 0.0624 (11) | 0.0790 (13) | 0.0556 (9) | −0.0043 (10) | 0.0044 (8) | −0.0159 (9) |
C3 | 0.0768 (13) | 0.0606 (11) | 0.0886 (14) | −0.0091 (9) | 0.0161 (11) | −0.0150 (10) |
C4 | 0.0764 (13) | 0.0649 (12) | 0.0764 (12) | 0.0025 (9) | 0.0132 (10) | 0.0063 (9) |
C5 | 0.0598 (10) | 0.0658 (11) | 0.0493 (8) | 0.0043 (8) | 0.0053 (7) | 0.0069 (8) |
C6 | 0.0469 (8) | 0.0541 (9) | 0.0384 (7) | 0.0005 (7) | 0.0061 (6) | −0.0009 (6) |
C11 | 0.0712 (12) | 0.0939 (13) | 0.0321 (8) | 0.0072 (10) | −0.0035 (7) | 0.0014 (7) |
C12 | 0.0830 (13) | 0.0953 (14) | 0.0423 (9) | 0.0014 (11) | 0.0063 (9) | 0.0060 (8) |
C61 | 0.0614 (10) | 0.0727 (11) | 0.0345 (7) | −0.0054 (8) | −0.0054 (7) | −0.0006 (7) |
C62 | 0.0860 (14) | 0.0958 (14) | 0.0426 (9) | −0.0113 (11) | 0.0070 (9) | −0.0108 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.3785 (18) | C5—C6 | 1.367 (2) |
O1—C11 | 1.4107 (16) | C11—C12 | 1.454 (2) |
O2—C6 | 1.3748 (18) | C61—C62 | 1.458 (2) |
O2—C61 | 1.4139 (16) | C2—H2 | 0.9298 |
N1—C12 | 1.115 (3) | C3—H3 | 0.9300 |
N2—C62 | 1.120 (3) | C4—H4 | 0.9300 |
C1—C2 | 1.372 (2) | C5—H5 | 0.9299 |
C1—C6 | 1.3942 (18) | C11—H11A | 0.9699 |
C2—C3 | 1.383 (3) | C11—H11B | 0.9700 |
C3—C4 | 1.365 (3) | C61—H61A | 0.9702 |
C4—C5 | 1.378 (2) | C61—H61B | 0.9701 |
| | | |
O1···O2 | 2.5208 (13) | C62···N1vii | 3.313 (3) |
O1···C61i | 3.2871 (19) | C2···H11Aiv | 3.0468 |
O1···C62i | 3.285 (2) | C2···H11A | 2.5601 |
O2···C61i | 3.1658 (19) | C4···H4viii | 3.0640 |
O2···O1 | 2.5208 (13) | C5···H61A | 2.5708 |
O2···O2i | 3.0807 (14) | C11···H2 | 2.6003 |
O1···H61Bi | 2.5246 | C12···H2 | 2.9611 |
O2···H61Bi | 2.6388 | C61···H5 | 2.5468 |
N1···C61ii | 3.184 (3) | C62···H5 | 2.7889 |
N1···C62ii | 3.313 (3) | H2···C11 | 2.6003 |
N2···C11iii | 3.046 (3) | H2···C12 | 2.9611 |
N2···C12iii | 3.303 (3) | H2···H11A | 2.0823 |
N1···H61Aii | 2.6125 | H4···C4viii | 3.0640 |
N2···H11Aiii | 2.7336 | H4···H4viii | 2.4170 |
N2···H11Biii | 2.7399 | H5···C61 | 2.5468 |
C2···C12 | 3.341 (3) | H5···C62 | 2.7889 |
C5···C62 | 3.212 (2) | H5···H61A | 2.0972 |
C5···C6iv | 3.559 (2) | H11A···C2 | 2.5601 |
C6···C5v | 3.559 (2) | H11A···H2 | 2.0823 |
C11···N2vi | 3.046 (3) | H11A···C2v | 3.0468 |
C12···N2vi | 3.303 (3) | H11A···N2vi | 2.7336 |
C12···C2 | 3.341 (3) | H11B···N2vi | 2.7399 |
C61···N1vii | 3.184 (3) | H61A···C5 | 2.5708 |
C61···O2i | 3.1658 (19) | H61A···H5 | 2.0972 |
C61···O1i | 3.2871 (19) | H61A···N1vii | 2.6125 |
C62···C5 | 3.212 (2) | H61B···O1i | 2.5246 |
C62···O1i | 3.285 (2) | H61B···O2i | 2.6388 |
| | | |
C1—O1—C11 | 118.73 (12) | C3—C2—H2 | 120.38 |
C6—O2—C61 | 117.98 (11) | C2—C3—H3 | 119.62 |
O1—C1—C2 | 126.19 (13) | C4—C3—H3 | 119.60 |
O1—C1—C6 | 113.99 (13) | C3—C4—H4 | 119.89 |
C2—C1—C6 | 119.82 (14) | C5—C4—H4 | 119.87 |
C1—C2—C3 | 119.23 (15) | C4—C5—H5 | 120.20 |
C2—C3—C4 | 120.78 (18) | C6—C5—H5 | 120.21 |
C3—C4—C5 | 120.24 (17) | O1—C11—H11A | 109.64 |
C4—C5—C6 | 119.59 (14) | O1—C11—H11B | 109.63 |
O2—C6—C1 | 114.31 (13) | C12—C11—H11A | 109.63 |
O2—C6—C5 | 125.36 (12) | C12—C11—H11B | 109.63 |
C1—C6—C5 | 120.33 (14) | H11A—C11—H11B | 108.14 |
O1—C11—C12 | 110.15 (13) | O2—C61—H61A | 109.49 |
N1—C12—C11 | 177.8 (2) | O2—C61—H61B | 109.49 |
O2—C61—C62 | 110.78 (13) | C62—C61—H61A | 109.49 |
N2—C62—C61 | 178.2 (2) | C62—C61—H61B | 109.49 |
C1—C2—H2 | 120.38 | H61A—C61—H61B | 108.05 |
| | | |
C11—O1—C1—C2 | 2.2 (2) | O1—C1—C2—C3 | 178.65 (14) |
C11—O1—C1—C6 | −178.69 (12) | C2—C1—C6—O2 | −179.28 (13) |
C1—O1—C11—C12 | 83.15 (18) | C2—C1—C6—C5 | 0.7 (2) |
C61—O2—C6—C1 | −179.44 (12) | C1—C2—C3—C4 | 0.3 (2) |
C61—O2—C6—C5 | 0.5 (2) | C2—C3—C4—C5 | −0.4 (2) |
C6—O2—C61—C62 | 78.23 (17) | C3—C4—C5—C6 | 0.7 (2) |
C6—C1—C2—C3 | −0.4 (2) | C4—C5—C6—O2 | 179.18 (14) |
O1—C1—C6—O2 | 1.52 (18) | C4—C5—C6—C1 | −0.8 (2) |
O1—C1—C6—C5 | −178.45 (13) | | |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1/2, y, z+1/2; (iii) −x+3/2, y, z−1/2; (iv) x−1/2, −y+1/2, z; (v) x+1/2, −y+1/2, z; (vi) −x+3/2, y, z+1/2; (vii) −x+1/2, y, z−1/2; (viii) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C61—H61A···N1vii | 0.97 | 2.61 | 3.184 (3) | 118 |
C61—H61B···O1i | 0.97 | 2.52 | 3.2871 (19) | 135 |
Symmetry codes: (i) −x+1, −y, −z; (vii) −x+1/2, y, z−1/2. |