In the crystal structure of the title compound, C
11H
10N
2O
3, intramolecular C—H
O interactions and intermolecular C—H
N interactions help to stabilize the structure.
Supporting information
CCDC reference: 277186
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.113
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 5.38 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C22 .. 6.11 su
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 28.98
From the CIF: _reflns_number_total 2402
From the CIF: _diffrn_reflns_limit_ max hkl 35. 5. 22.
From the CIF: _diffrn_reflns_limit_ min hkl -35. -5. -22.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 37. 6. 23.
Calculated minimum hkl -37. -6. -23.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 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: WinGX (Farrugia, 1999).
(2-Cyanomethoxy-6-methoxyphenoxy)acetonitrile
top
Crystal data top
C11H10N2O3 | F(000) = 912 |
Mr = 218.21 | Dx = 1.299 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 13819 reflections |
a = 27.871 (2) Å | θ = 2.1–27.1° |
b = 4.6083 (3) Å | µ = 0.10 mm−1 |
c = 17.3806 (15) Å | T = 296 K |
β = 90.949 (7)° | Prism, colourless |
V = 2232.0 (3) Å3 | 0.47 × 0.30 × 0.13 mm |
Z = 8 | |
Data collection top
Stoe IPDS-II diffractometer | 2402 independent reflections |
Radiation source: fine-focus sealed tube | 1520 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 6.67 pixels mm-1 | θmax = 29.0°, θmin = 2.3° |
ω scans | h = −35→35 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −5→5 |
Tmin = 0.996, Tmax = 0.999 | l = −22→22 |
16223 measured 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0691P)2] where P = (Fo2 + 2Fc2)/3 |
2402 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | |
O21 | 0.44253 (4) | 0.1358 (2) | 0.43728 (6) | 0.0514 (3) | |
O11 | 0.37088 (4) | 0.4094 (2) | 0.34546 (6) | 0.0556 (3) | |
C1 | 0.35702 (6) | 0.2304 (3) | 0.40136 (8) | 0.0476 (4) | |
O31 | 0.42570 (5) | −0.2291 (3) | 0.54849 (7) | 0.0701 (4) | |
C2 | 0.39494 (5) | 0.0835 (3) | 0.44705 (8) | 0.0457 (4) | |
C3 | 0.38573 (6) | −0.1006 (4) | 0.50647 (9) | 0.0541 (4) | |
C4 | 0.33816 (7) | −0.1350 (4) | 0.51880 (11) | 0.0693 (5) | |
H4 | 0.3286 | −0.2575 | 0.5582 | 0.083* | |
C22 | 0.44838 (6) | −0.1080 (4) | 0.31842 (11) | 0.0610 (5) | |
C6 | 0.30975 (6) | 0.1957 (4) | 0.41398 (11) | 0.0603 (5) | |
H6 | 0.2857 | 0.2879 | 0.3854 | 0.072* | |
C11 | 0.33361 (6) | 0.5468 (4) | 0.29258 (11) | 0.0594 (4) | |
H11A | 0.3493 | 0.6937 | 0.2619 | 0.071* | |
H11B | 0.3101 | 0.6445 | 0.3240 | 0.071* | |
C12 | 0.30679 (6) | 0.3381 (4) | 0.23769 (11) | 0.0603 (5) | |
C5 | 0.30124 (7) | 0.0124 (4) | 0.47263 (12) | 0.0708 (6) | |
H5 | 0.2694 | −0.0230 | 0.4847 | 0.085* | |
C21 | 0.46502 (6) | −0.0969 (4) | 0.40281 (9) | 0.0559 (4) | |
H21A | 0.4566 | −0.2759 | 0.4287 | 0.067* | |
H21B | 0.4996 | −0.0732 | 0.4060 | 0.067* | |
C31 | 0.41895 (9) | −0.4132 (5) | 0.61243 (11) | 0.0842 (7) | |
H31A | 0.4496 | −0.4766 | 0.6321 | 0.126* | |
H31B | 0.4003 | −0.5787 | 0.5968 | 0.126* | |
H31C | 0.4024 | −0.3093 | 0.6518 | 0.126* | |
N11 | 0.28675 (6) | 0.1759 (5) | 0.19501 (10) | 0.0841 (5) | |
N22 | 0.43502 (8) | −0.1182 (4) | 0.25337 (11) | 0.0939 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O21 | 0.0450 (6) | 0.0513 (6) | 0.0581 (6) | −0.0050 (5) | 0.0082 (5) | −0.0045 (5) |
O11 | 0.0457 (6) | 0.0559 (7) | 0.0652 (7) | −0.0028 (5) | 0.0072 (5) | 0.0085 (6) |
C1 | 0.0490 (9) | 0.0429 (8) | 0.0511 (8) | −0.0065 (7) | 0.0109 (7) | −0.0072 (7) |
O31 | 0.0824 (9) | 0.0702 (8) | 0.0580 (7) | −0.0004 (7) | 0.0105 (6) | 0.0138 (6) |
C2 | 0.0450 (8) | 0.0446 (8) | 0.0479 (8) | −0.0067 (7) | 0.0079 (6) | −0.0096 (7) |
C3 | 0.0643 (10) | 0.0493 (9) | 0.0491 (8) | −0.0047 (8) | 0.0119 (7) | −0.0062 (7) |
C4 | 0.0813 (13) | 0.0623 (11) | 0.0653 (10) | −0.0168 (10) | 0.0314 (9) | −0.0051 (9) |
C22 | 0.0599 (10) | 0.0625 (11) | 0.0613 (11) | −0.0039 (9) | 0.0194 (8) | −0.0033 (9) |
C6 | 0.0467 (9) | 0.0602 (10) | 0.0744 (11) | −0.0014 (8) | 0.0136 (8) | −0.0090 (9) |
C11 | 0.0552 (10) | 0.0512 (9) | 0.0717 (11) | 0.0014 (8) | 0.0012 (8) | 0.0065 (8) |
C12 | 0.0493 (9) | 0.0708 (12) | 0.0609 (10) | −0.0003 (9) | 0.0065 (8) | 0.0035 (10) |
C5 | 0.0614 (11) | 0.0707 (12) | 0.0814 (13) | −0.0133 (10) | 0.0324 (10) | −0.0105 (10) |
C21 | 0.0460 (9) | 0.0617 (10) | 0.0603 (10) | 0.0044 (8) | 0.0071 (7) | −0.0023 (8) |
C31 | 0.130 (2) | 0.0669 (12) | 0.0561 (10) | 0.0016 (13) | 0.0173 (11) | 0.0103 (10) |
N11 | 0.0729 (11) | 0.1051 (14) | 0.0745 (10) | −0.0152 (11) | 0.0090 (9) | −0.0118 (11) |
N22 | 0.1202 (16) | 0.1004 (15) | 0.0618 (11) | −0.0054 (12) | 0.0223 (10) | −0.0067 (10) |
Geometric parameters (Å, º) top
O21—C2 | 1.3614 (18) | C22—C21 | 1.532 (3) |
O21—C21 | 1.3837 (19) | C6—C5 | 1.348 (3) |
O11—C1 | 1.3364 (18) | C6—H6 | 0.9300 |
O11—C11 | 1.514 (2) | C11—C12 | 1.539 (3) |
C1—C6 | 1.349 (2) | C11—H11A | 0.9700 |
C1—C2 | 1.476 (2) | C11—H11B | 0.9700 |
O31—C31 | 1.413 (2) | C12—N11 | 1.186 (2) |
O31—C3 | 1.449 (2) | C5—H5 | 0.9300 |
C2—C3 | 1.364 (2) | C21—H21A | 0.9700 |
C3—C4 | 1.356 (3) | C21—H21B | 0.9700 |
C4—C5 | 1.462 (3) | C31—H31A | 0.9600 |
C4—H4 | 0.9300 | C31—H31B | 0.9600 |
C22—N22 | 1.186 (2) | C31—H31C | 0.9600 |
| | | |
C2—O21—C21 | 111.46 (12) | C12—C11—H11A | 108.3 |
C1—O11—C11 | 119.70 (12) | O11—C11—H11B | 108.3 |
O11—C1—C6 | 119.11 (15) | C12—C11—H11B | 108.3 |
O11—C1—C2 | 117.47 (13) | H11A—C11—H11B | 107.4 |
C6—C1—C2 | 123.42 (15) | N11—C12—C11 | 179.04 (19) |
C31—O31—C3 | 122.05 (15) | C6—C5—C4 | 125.13 (17) |
O21—C2—C3 | 113.62 (15) | C6—C5—H5 | 117.4 |
O21—C2—C1 | 122.82 (13) | C4—C5—H5 | 117.4 |
C3—C2—C1 | 123.40 (14) | O21—C21—C22 | 107.96 (14) |
C4—C3—C2 | 112.92 (17) | O21—C21—H21A | 110.1 |
C4—C3—O31 | 128.19 (16) | C22—C21—H21A | 110.1 |
C2—C3—O31 | 118.88 (14) | O21—C21—H21B | 110.1 |
C3—C4—C5 | 122.69 (16) | C22—C21—H21B | 110.1 |
C3—C4—H4 | 118.7 | H21A—C21—H21B | 108.4 |
C5—C4—H4 | 118.7 | O31—C31—H31A | 109.5 |
N22—C22—C21 | 179.2 (2) | O31—C31—H31B | 109.5 |
C5—C6—C1 | 112.45 (18) | H31A—C31—H31B | 109.5 |
C5—C6—H6 | 123.8 | O31—C31—H31C | 109.5 |
C1—C6—H6 | 123.8 | H31A—C31—H31C | 109.5 |
O11—C11—C12 | 115.87 (13) | H31B—C31—H31C | 109.5 |
O11—C11—H11A | 108.3 | | |
| | | |
C11—O11—C1—C6 | −5.9 (2) | C1—C2—C3—O31 | −178.84 (13) |
C11—O11—C1—C2 | 175.00 (13) | C31—O31—C3—C4 | −1.3 (3) |
C21—O21—C2—C3 | 75.86 (16) | C31—O31—C3—C2 | 177.65 (15) |
C21—O21—C2—C1 | −108.63 (15) | C2—C3—C4—C5 | −0.2 (2) |
O11—C1—C2—O21 | 3.8 (2) | O31—C3—C4—C5 | 178.89 (16) |
C6—C1—C2—O21 | −175.28 (15) | O11—C1—C6—C5 | −179.15 (15) |
O11—C1—C2—C3 | 178.88 (13) | C2—C1—C6—C5 | −0.1 (2) |
C6—C1—C2—C3 | −0.2 (2) | C1—O11—C11—C12 | −67.87 (19) |
O21—C2—C3—C4 | 175.78 (14) | C1—C6—C5—C4 | 0.2 (3) |
C1—C2—C3—C4 | 0.3 (2) | C3—C4—C5—C6 | −0.1 (3) |
O21—C2—C3—O31 | −3.4 (2) | C2—O21—C21—C22 | 71.61 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21A···O31 | 0.97 | 2.28 | 2.842 (2) | 116 |
C11—H11A···N22i | 0.97 | 2.55 | 3.302 (3) | 135 |
Symmetry code: (i) x, y+1, z. |