2-[2-(Cyano­methoxy)­phenoxy]­aceto­nitrile

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.

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

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Computing details

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

Crystal data

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) Å^3	Prism, colourless
Z = 8	0.35 × 0.30 × 0.20 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: Full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 0.73	w = 1/[σ^2(Fo^2) + (0.049P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···N1^vii	3.313 (3)
O1···C61^i	3.2871 (19)	C2···H11A^iv	3.0468
O1···C62^i	3.285 (2)	C2···H11A	2.5601
O2···C61^i	3.1658 (19)	C4···H4^viii	3.0640
O2···O1	2.5208 (13)	C5···H61A	2.5708
O2···O2^i	3.0807 (14)	C11···H2	2.6003
O1···H61B^i	2.5246	C12···H2	2.9611
O2···H61B^i	2.6388	C61···H5	2.5468
N1···C61^ii	3.184 (3)	C62···H5	2.7889
N1···C62^ii	3.313 (3)	H2···C11	2.6003
N2···C11^iii	3.046 (3)	H2···C12	2.9611
N2···C12^iii	3.303 (3)	H2···H11A	2.0823
N1···H61A^ii	2.6125	H4···C4^viii	3.0640
N2···H11A^iii	2.7336	H4···H4^viii	2.4170
N2···H11B^iii	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···C6^iv	3.559 (2)	H11A···C2	2.5601
C6···C5^v	3.559 (2)	H11A···H2	2.0823
C11···N2^vi	3.046 (3)	H11A···C2^v	3.0468
C12···N2^vi	3.303 (3)	H11A···N2^vi	2.7336
C12···C2	3.341 (3)	H11B···N2^vi	2.7399
C61···N1^vii	3.184 (3)	H61A···C5	2.5708
C61···O2^i	3.1658 (19)	H61A···H5	2.0972
C61···O1^i	3.2871 (19)	H61A···N1^vii	2.6125
C62···C5	3.212 (2)	H61B···O1^i	2.5246
C62···O1^i	3.285 (2)	H61B···O2^i	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)

D—H···A	D—H	H···A	D···A	D—H···A
C61—H61A···N1^vii	0.97	2.61	3.184 (3)	118
C61—H61B···O1^i	0.97	2.52	3.2871 (19)	135

Symmetry codes: (i) −x+1, −y, −z; (vii) −x+1/2, y, z−1/2.