2-(Cyanomethoxy)benzonitrile

In the title compound, C₉H₆N₂O, two independent and almost identical mol­ecules, pseudosymmetrically related by twofold rotation, form the asymmetric unit. The mol­ecules adopt an overall L-shaped structure in which the cyano­meth­oxy residue is approximately perpendicular to the benzonitrile plane. The mol­ecules assemble into dimers via C—H...N and C—H...O inter­actions, forming a sheet structure approximately in the (404) plane. Noteworthy π–π inter­actions result in two distinct types of offset π-stacking arrangements.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.067
• wR factor = 0.170
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2A    -   C9A    ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2B    -   C9B    ...       1.43 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

2-(Cyanomethoxy)benzonitrile

Crystal data

C9H6N2O	Z = 4
Mr = 158.16	F(000) = 328
Triclinic, P1	Dx = 1.259 Mg m^−3
Hall symbol: -P 1	Melting point: 62(2) K
a = 7.4807 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7018 (8) Å	Cell parameters from 1535 reflections
c = 15.8021 (17) Å	θ = 2.5–25°
α = 86.934 (2)°	µ = 0.09 mm^−1
β = 85.235 (2)°	T = 295 K
γ = 66.910 (3)°	Needle, colorless
V = 834.39 (15) Å^3	0.28 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2887 independent reflections
Radiation source: fine-focus sealed tube	1551 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.970, Tmax = 0.986	k = −8→9
5850 measured reflections	l = −18→18

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)] = 0.067	Hydrogen site location: difference Fourier map
wR(F^2) = 0.170	All H-atom parameters refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0772P)^2] where P = (Fo^2 + 2Fc^2)/3
2887 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d

Plane 1 m1 = -0.83642(0.00045) m2 = 0.47022(0.00073) m3 = -0.28159(0.00072) D = -1.41365(0.00331) Atom d s d/s (d/s)**2 C1A * -0.0039 0.0031 - 1.262 1.593 C2A * -0.0006 0.0031 - 0.206 0.043 C3A * -0.0036 0.0042 - 0.857 0.734 C4A * 0.0003 0.0049 0.067 0.004 C5A * 0.0067 0.0047 1.434 2.057 C6A * 0.0077 0.0039 1.944 3.779 C7A * 0.0368 0.0042 8.717 75.978 C9A * 0.0018 0.0038 0.476 0.226 O1A * -0.0163 0.0022 - 7.417 55.012 N2A * 0.0160 0.0039 4.100 16.811 C8A 1.3949 0.0047 298.431 89061.047 N1A 2.4715 0.0047 529.819 280708.594 ============ Sum((d/s)**2) for starred atoms 156.237 Chi-squared at 95% for 7 degrees of freedom: 14.10 The group of atoms deviates significantly from planarity

Plane 2 m1 = -0.93772(0.00027) m2 = 0.26905(0.00072) m3 = -0.21976(0.00074) D = -8.01816(0.00585) Atom d s d/s (d/s)**2 C1B * 0.0015 0.0030 0.488 0.238 C2B * -0.0052 0.0030 - 1.702 2.897 C3B * -0.0144 0.0038 - 3.768 14.201 C4B * -0.0011 0.0044 - 0.249 0.062 C5B * 0.0091 0.0043 2.096 4.392 C6B * 0.0142 0.0037 3.885 15.094 C7B * 0.0143 0.0040 3.593 12.910 C9B * 0.0055 0.0035 1.565 2.450 O1B * -0.0125 0.0022 - 5.691 32.387 N2B * 0.0125 0.0033 3.776 14.261 C8B 1.3619 0.0041 329.823 108783.250 N1B 2.4139 0.0037 655.275 429385.344 ============ Sum((d/s)**2) for starred atoms 98.892 Chi-squared at 95% for 7 degrees of freedom: 14.10 The group of atoms deviates significantly from planarity

Plane 3 m1 = -0.15678(0.00159) m2 = 0.57389(0.00179) m3 = 0.80378(0.00152) D = 3.42916(0.00325) Atom d s d/s (d/s)**2 C7A * 0.0000 0.0040 0.000 0.000 C9A * 0.0000 0.0038 0.000 0.000 N1A * 0.0000 0.0040 0.000 0.000 O1A -0.0770 0.0020 - 38.668 1495.197 ============ Sum((d/s)**2) for starred atoms 0.000

Plane 4 m1 = -0.14363(0.00246) m2 = -0.46872(0.00071) m3 = -0.87159(0.00053) D = -7.94758(0.01606) Atom d s d/s (d/s)**2 C7B * 0.0000 0.0040 0.000 0.000 C9B * 0.0000 0.0033 0.000 0.000 N1B * 0.0000 0.0031 0.000 0.000 O1B -0.0738 0.0020 - 37.001 1369.082 ============ Sum((d/s)**2) for starred atoms 0.000 Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 13.41 (0.05) 166.59 (0.05) 1 3 79.94 (0.10) 100.06 (0.10) 1 4 81.65 (0.13) 98.35 (0.13) 2 3 82.83 (0.10) 97.17 (0.10) 2 4 78.46 (0.14) 101.54 (0.14) 3 4 18.73 (0.16) 161.27 (0.16)

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 (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.1103 (3)	0.3160 (3)	0.18541 (13)	0.0630 (7)
N1A	−0.2943 (6)	0.2248 (6)	0.1799 (2)	0.1147 (13)
N2A	0.1783 (5)	0.7235 (5)	0.1612 (2)	0.0937 (11)
C1A	0.1776 (4)	0.2959 (4)	0.10160 (19)	0.0500 (8)
C2A	0.2251 (4)	0.4438 (4)	0.0677 (2)	0.0512 (8)
C3A	0.2974 (5)	0.4390 (7)	−0.0168 (2)	0.0701 (10)
C4A	0.3193 (5)	0.2893 (8)	−0.0656 (3)	0.0863 (13)
C5A	0.2704 (5)	0.1454 (7)	−0.0313 (3)	0.0817 (12)
C6A	0.1987 (5)	0.1479 (5)	0.0525 (2)	0.0677 (10)
C7A	0.0493 (5)	0.1757 (5)	0.2257 (3)	0.0647 (10)
C8A	−0.1426 (6)	0.2005 (5)	0.2000 (2)	0.0758 (11)
C9A	0.2001 (5)	0.5985 (5)	0.1196 (2)	0.0636 (9)
H3A	0.319 (5)	0.554 (5)	−0.040 (2)	0.094 (12)*
H4A	0.365 (5)	0.287 (5)	−0.121 (2)	0.088 (12)*
H5A	0.290 (5)	0.037 (5)	−0.063 (2)	0.089 (13)*
H6A	0.162 (4)	0.052 (4)	0.0743 (19)	0.071 (11)*
H7A1	0.143 (4)	0.049 (4)	0.2095 (17)	0.056 (8)*
H7A2	0.048 (5)	0.195 (5)	0.292 (2)	0.108 (14)*
O1B	0.8353 (3)	0.5137 (3)	0.36901 (13)	0.0595 (6)
N1B	0.4922 (5)	0.9019 (4)	0.2864 (2)	0.0887 (10)
N2B	0.8635 (4)	0.0672 (4)	0.41053 (19)	0.0744 (9)
C1B	0.7751 (4)	0.5345 (4)	0.4537 (2)	0.0477 (8)
C2B	0.7708 (4)	0.3709 (4)	0.4947 (2)	0.0498 (8)
C3B	0.7154 (4)	0.3726 (6)	0.5810 (2)	0.0676 (10)
C4B	0.6630 (5)	0.5374 (7)	0.6248 (3)	0.0809 (12)
C5B	0.6679 (5)	0.6969 (7)	0.5830 (3)	0.0771 (12)
C6B	0.7230 (4)	0.6976 (5)	0.4977 (2)	0.0620 (9)
C7B	0.8421 (5)	0.6739 (5)	0.3205 (3)	0.0621 (10)
C8B	0.6454 (5)	0.8041 (4)	0.3012 (2)	0.0601 (9)
C9B	0.8223 (4)	0.2022 (5)	0.4478 (2)	0.0553 (9)
H3B	0.710 (4)	0.245 (5)	0.608 (2)	0.090 (11)*
H4B	0.628 (5)	0.536 (5)	0.684 (2)	0.097 (13)*
H5B	0.643 (5)	0.810 (5)	0.616 (2)	0.094 (13)*
H6B	0.728 (4)	0.812 (5)	0.469 (2)	0.083 (11)*
H7B1	0.900 (4)	0.743 (4)	0.3514 (19)	0.065 (10)*
H7B2	0.914 (6)	0.623 (5)	0.260 (3)	0.114 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0864 (16)	0.0524 (13)	0.0570 (15)	−0.0378 (11)	0.0164 (11)	−0.0066 (11)
N1A	0.100 (3)	0.143 (3)	0.115 (3)	−0.064 (3)	−0.010 (2)	0.025 (2)
N2A	0.128 (3)	0.069 (2)	0.102 (3)	−0.061 (2)	0.006 (2)	−0.001 (2)
C1A	0.0502 (17)	0.0451 (18)	0.052 (2)	−0.0160 (14)	0.0012 (14)	−0.0074 (16)
C2A	0.0452 (17)	0.0520 (19)	0.055 (2)	−0.0182 (14)	−0.0006 (14)	0.0026 (16)
C3A	0.059 (2)	0.092 (3)	0.057 (3)	−0.028 (2)	−0.0019 (17)	0.013 (2)
C4A	0.069 (2)	0.127 (4)	0.054 (3)	−0.029 (2)	0.004 (2)	−0.008 (3)
C5A	0.074 (3)	0.083 (3)	0.076 (3)	−0.015 (2)	0.001 (2)	−0.032 (3)
C6A	0.074 (2)	0.057 (2)	0.069 (3)	−0.0214 (19)	0.0071 (19)	−0.015 (2)
C7A	0.078 (3)	0.048 (2)	0.073 (3)	−0.0324 (19)	0.002 (2)	0.0113 (19)
C8A	0.088 (3)	0.073 (2)	0.075 (3)	−0.044 (2)	0.001 (2)	0.014 (2)
C9A	0.071 (2)	0.056 (2)	0.072 (3)	−0.0354 (19)	0.0010 (18)	0.009 (2)
O1B	0.0704 (14)	0.0422 (12)	0.0622 (15)	−0.0207 (10)	0.0097 (11)	−0.0010 (10)
N1B	0.085 (2)	0.073 (2)	0.097 (3)	−0.0197 (18)	−0.0136 (19)	0.0067 (18)
N2B	0.096 (2)	0.0451 (17)	0.082 (2)	−0.0290 (16)	−0.0022 (17)	0.0075 (16)
C1B	0.0400 (16)	0.0466 (18)	0.056 (2)	−0.0165 (13)	−0.0007 (13)	−0.0048 (16)
C2B	0.0408 (16)	0.0484 (19)	0.060 (2)	−0.0170 (14)	−0.0028 (14)	0.0012 (17)
C3B	0.052 (2)	0.081 (3)	0.065 (3)	−0.0218 (18)	−0.0031 (16)	0.011 (2)
C4B	0.063 (2)	0.108 (4)	0.058 (3)	−0.019 (2)	0.0001 (19)	−0.012 (3)
C5B	0.064 (2)	0.081 (3)	0.080 (3)	−0.017 (2)	−0.013 (2)	−0.029 (3)
C6B	0.058 (2)	0.057 (2)	0.070 (3)	−0.0200 (17)	−0.0015 (17)	−0.014 (2)
C7B	0.066 (2)	0.0424 (19)	0.078 (3)	−0.0247 (18)	0.0083 (19)	0.0060 (18)
C8B	0.075 (2)	0.0431 (18)	0.061 (2)	−0.0239 (18)	0.0055 (17)	0.0008 (16)
C9B	0.0567 (19)	0.046 (2)	0.066 (2)	−0.0247 (17)	−0.0058 (16)	0.0138 (18)

Geometric parameters (Å, º)

O1A—C1A	1.372 (3)	O1B—C1B	1.373 (3)
O1A—C7A	1.431 (3)	O1B—C7B	1.433 (3)
N1A—C8A	1.145 (5)	N1B—C8B	1.133 (4)
N2A—C9A	1.145 (4)	N2B—C9B	1.143 (4)
C1A—C6A	1.364 (4)	C1B—C6B	1.370 (4)
C1A—C2A	1.390 (4)	C1B—C2B	1.396 (4)
C2A—C3A	1.395 (4)	C2B—C3B	1.392 (4)
C2A—C9A	1.425 (5)	C2B—C9B	1.431 (4)
C3A—C4A	1.370 (6)	C3B—C4B	1.379 (5)
C3A—H3A	1.01 (4)	C3B—H3B	1.06 (3)
C4A—C5A	1.370 (6)	C4B—C5B	1.375 (6)
C4A—H4A	0.92 (4)	C4B—H4B	0.95 (4)
C5A—C6A	1.385 (5)	C5B—C6B	1.378 (5)
C5A—H5A	0.95 (4)	C5B—H5B	0.98 (4)
C6A—H6A	0.92 (3)	C6B—H6B	0.98 (3)
C7A—C8A	1.461 (5)	C7B—C8B	1.465 (5)
C7A—H7A1	0.98 (3)	C7B—H7B1	0.97 (3)
C7A—H7A2	1.06 (4)	C7B—H7B2	1.07 (4)
C1A—O1A—C7A	118.7 (3)	C1B—O1B—C7B	118.8 (3)
C6A—C1A—O1A	125.5 (3)	C6B—C1B—O1B	125.3 (3)
C6A—C1A—C2A	120.4 (3)	C6B—C1B—C2B	120.4 (3)
O1A—C1A—C2A	114.1 (3)	O1B—C1B—C2B	114.3 (3)
C1A—C2A—C3A	119.6 (4)	C3B—C2B—C1B	119.9 (3)
C1A—C2A—C9A	119.8 (3)	C3B—C2B—C9B	120.1 (3)
C3A—C2A—C9A	120.6 (3)	C1B—C2B—C9B	120.0 (3)
C4A—C3A—C2A	119.6 (4)	C4B—C3B—C2B	119.3 (4)
C4A—C3A—H3A	123 (2)	C4B—C3B—H3B	124.6 (18)
C2A—C3A—H3A	117 (2)	C2B—C3B—H3B	116.0 (18)
C3A—C4A—C5A	120.0 (4)	C5B—C4B—C3B	119.8 (4)
C3A—C4A—H4A	119 (2)	C5B—C4B—H4B	121 (2)
C5A—C4A—H4A	121 (2)	C3B—C4B—H4B	119 (2)
C4A—C5A—C6A	121.1 (5)	C4B—C5B—C6B	121.7 (4)
C4A—C5A—H5A	122 (2)	C4B—C5B—H5B	119 (2)
C6A—C5A—H5A	117 (2)	C6B—C5B—H5B	119 (2)
C1A—C6A—C5A	119.3 (4)	C1B—C6B—C5B	118.9 (4)
C1A—C6A—H6A	120 (2)	C1B—C6B—H6B	120.1 (19)
C5A—C6A—H6A	120 (2)	C5B—C6B—H6B	120.9 (19)
O1A—C7A—C8A	110.6 (3)	O1B—C7B—C8B	110.5 (3)
O1A—C7A—H7A1	109.9 (15)	O1B—C7B—H7B1	111.2 (18)
C8A—C7A—H7A1	108.7 (16)	C8B—C7B—H7B1	108.0 (18)
O1A—C7A—H7A2	105 (2)	O1B—C7B—H7B2	107 (2)
C8A—C7A—H7A2	111.9 (19)	C8B—C7B—H7B2	105 (2)
H7A1—C7A—H7A2	111 (3)	H7B1—C7B—H7B2	115 (3)
N1A—C8A—C7A	178.3 (4)	N1B—C8B—C7B	178.6 (3)
N2A—C9A—C2A	179.4 (4)	N2B—C9B—C2B	179.9 (4)
C7A—O1A—C1A—C6A	−2.5 (4)	C7B—O1B—C1B—C6B	−1.3 (4)
C7A—O1A—C1A—C2A	177.4 (3)	C7B—O1B—C1B—C2B	179.0 (3)
C6A—C1A—C2A—C3A	−0.9 (4)	C6B—C1B—C2B—C3B	−0.7 (4)
O1A—C1A—C2A—C3A	179.3 (2)	O1B—C1B—C2B—C3B	179.0 (2)
C6A—C1A—C2A—C9A	179.3 (3)	C6B—C1B—C2B—C9B	178.9 (3)
O1A—C1A—C2A—C9A	−0.5 (4)	O1B—C1B—C2B—C9B	−1.4 (4)
C1A—C2A—C3A—C4A	0.5 (5)	C1B—C2B—C3B—C4B	0.8 (4)
C9A—C2A—C3A—C4A	−179.7 (3)	C9B—C2B—C3B—C4B	−178.9 (3)
C2A—C3A—C4A—C5A	0.0 (5)	C2B—C3B—C4B—C5B	−0.6 (5)
C3A—C4A—C5A—C6A	−0.1 (6)	C3B—C4B—C5B—C6B	0.4 (6)
O1A—C1A—C6A—C5A	−179.4 (3)	O1B—C1B—C6B—C5B	−179.1 (3)
C2A—C1A—C6A—C5A	0.8 (5)	C2B—C1B—C6B—C5B	0.5 (4)
C4A—C5A—C6A—C1A	−0.3 (6)	C4B—C5B—C6B—C1B	−0.4 (5)
C1A—O1A—C7A—C8A	−76.7 (4)	C1B—O1B—C7B—C8B	−75.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7A1···N2A^i	0.98 (3)	2.57 (3)	3.418 (5)	145 (2)
C7A—H7A2···N2B^ii	1.06 (3)	2.61 (4)	3.337 (5)	125 (3)
C7B—H7B1···N2B^iii	0.98 (3)	2.62 (3)	3.479 (5)	147 (2)
C7B—H7B2···O1A^iv	1.07 (5)	2.53 (4)	3.429 (5)	141 (3)
C5B—H5B···N1B^v	0.99 (4)	2.58 (3)	3.551 (6)	167 (3)

Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) x, y+1, z; (iv) x+1, y, z; (v) −x+1, −y+2, −z+1.