4-(Benz­yloxy)-2-fluoro­benzonitrile

In the mol­ecule of the title compound, C₁₄H₁₀FNO, the dihedral angle between the planar rings is 68.87 (4)°. The crystal structure is stabilized by C—H...π inter­ations and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.074
• wR factor = 0.244
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.14
PLAT230_ALERT_2_C Hirshfeld Test Diff for    F1     -   C12     ..       5.12 su
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  C11    -   C14    ...       1.44 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

4-(Benzyloxy)-2-fluorobenzonitrile

Crystal data

C14H10FNO	F(000) = 944
Mr = 227.23	Dx = 1.326 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1725 reflections
a = 23.420 (3) Å	θ = 2.6–25.8°
b = 7.9307 (11) Å	µ = 0.10 mm^−1
c = 12.6046 (18) Å	T = 294 K
β = 103.433 (2)°	Block, colorless
V = 2277.1 (5) Å^3	0.32 × 0.28 × 0.12 mm
Z = 8

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2245 independent reflections
Radiation source: fine-focus sealed tube	1605 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 1.8°
ω scans	h = −26→28
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→8
Tmin = 0.970, Tmax = 0.989	l = −15→15
6209 measured 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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.244	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.1426P)^2 + 2.351P] where P = (Fo^2 + 2Fc^2)/3
2245 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.68 e Å^−3
0 restraints	Δρmin = −0.32 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.

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
F1	0.52543 (9)	0.3536 (3)	0.1085 (2)	0.0892 (8)
O1	0.34866 (9)	0.0708 (3)	0.07484 (16)	0.0546 (6)
N1	0.57290 (14)	0.3246 (4)	−0.1349 (3)	0.0822 (10)
C1	0.20420 (13)	0.0079 (4)	0.0497 (2)	0.0532 (7)
H1A	0.1950	0.0738	−0.0130	0.064*
C2	0.16323 (14)	−0.0141 (4)	0.1108 (3)	0.0617 (8)
H2A	0.1265	0.0361	0.0895	0.074*
C3	0.17698 (15)	−0.1110 (5)	0.2038 (3)	0.0670 (9)
H3A	0.1496	−0.1247	0.2461	0.080*
C4	0.23061 (15)	−0.1874 (4)	0.2345 (3)	0.0650 (9)
H4A	0.2391	−0.2548	0.2966	0.078*
C5	0.27222 (13)	−0.1653 (4)	0.1741 (3)	0.0570 (8)
H5A	0.3089	−0.2160	0.1958	0.068*
C6	0.25873 (12)	−0.0660 (3)	0.0800 (2)	0.0460 (7)
C7	0.30359 (13)	−0.0403 (4)	0.0135 (2)	0.0542 (8)
H7A	0.3207	−0.1476	0.0005	0.065*
H7B	0.2854	0.0099	−0.0563	0.065*
C8	0.39287 (12)	0.1117 (3)	0.0275 (2)	0.0469 (7)
C9	0.39617 (13)	0.0641 (4)	−0.0781 (2)	0.0549 (8)
H9A	0.3671	−0.0034	−0.1206	0.066*
C10	0.44284 (15)	0.1184 (4)	−0.1181 (3)	0.0586 (8)
H10A	0.4451	0.0856	−0.1878	0.070*
C11	0.48656 (13)	0.2204 (4)	−0.0578 (3)	0.0524 (7)
C12	0.48222 (12)	0.2619 (4)	0.0478 (2)	0.0529 (7)
C13	0.43707 (12)	0.2119 (4)	0.0902 (2)	0.0527 (7)
H13A	0.4354	0.2439	0.1605	0.063*
C14	0.53523 (14)	0.2788 (4)	−0.1001 (3)	0.0602 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0644 (13)	0.1072 (17)	0.0958 (16)	−0.0262 (12)	0.0180 (11)	−0.0267 (13)
O1	0.0508 (12)	0.0587 (12)	0.0574 (12)	−0.0138 (9)	0.0187 (9)	−0.0121 (9)
N1	0.0659 (19)	0.100 (2)	0.089 (2)	−0.0161 (17)	0.0355 (18)	−0.0085 (18)
C1	0.0515 (17)	0.0481 (15)	0.0562 (17)	−0.0046 (13)	0.0044 (13)	0.0051 (12)
C2	0.0420 (16)	0.0640 (19)	0.078 (2)	−0.0025 (14)	0.0111 (14)	−0.0019 (16)
C3	0.063 (2)	0.074 (2)	0.070 (2)	−0.0200 (17)	0.0270 (17)	−0.0057 (17)
C4	0.078 (2)	0.065 (2)	0.0499 (17)	−0.0098 (17)	0.0092 (16)	0.0109 (14)
C5	0.0509 (17)	0.0542 (17)	0.0603 (18)	0.0008 (13)	0.0017 (14)	0.0047 (13)
C6	0.0456 (15)	0.0396 (14)	0.0511 (15)	−0.0067 (11)	0.0081 (12)	−0.0044 (11)
C7	0.0510 (17)	0.0549 (17)	0.0578 (17)	−0.0102 (13)	0.0148 (13)	−0.0106 (13)
C8	0.0436 (15)	0.0425 (14)	0.0549 (16)	−0.0004 (11)	0.0122 (12)	−0.0020 (11)
C9	0.0560 (17)	0.0538 (17)	0.0547 (17)	−0.0095 (13)	0.0124 (13)	−0.0065 (13)
C10	0.068 (2)	0.0585 (18)	0.0543 (17)	−0.0026 (15)	0.0245 (15)	−0.0065 (13)
C11	0.0494 (16)	0.0473 (15)	0.0630 (18)	0.0019 (12)	0.0181 (13)	0.0019 (13)
C12	0.0406 (15)	0.0530 (16)	0.0638 (18)	−0.0041 (12)	0.0096 (13)	−0.0066 (13)
C13	0.0492 (16)	0.0549 (17)	0.0548 (17)	−0.0045 (13)	0.0138 (13)	−0.0109 (13)
C14	0.0535 (18)	0.0625 (19)	0.067 (2)	−0.0019 (14)	0.0198 (15)	−0.0051 (15)

Geometric parameters (Å, º)

F1—C12	1.334 (3)	C6—C7	1.502 (4)
O1—C7	1.452 (3)	C7—H7A	0.9700
O1—C8	1.350 (3)	C7—H7B	0.9700
C1—C2	1.374 (4)	C8—C13	1.396 (4)
C1—H1A	0.9300	C8—C9	1.403 (4)
C2—H2A	0.9300	C9—C10	1.375 (4)
C3—C4	1.367 (5)	C9—H9A	0.9300
C3—C2	1.376 (5)	C10—H10A	0.9300
C3—H3A	0.9300	C11—C10	1.386 (4)
C4—H4A	0.9300	C11—C14	1.442 (4)
C5—C4	1.380 (4)	C12—C11	1.397 (4)
C5—H5A	0.9300	C13—C12	1.351 (4)
C6—C1	1.376 (4)	C13—H13A	0.9300
C6—C5	1.397 (4)	C14—N1	1.132 (4)
C8—O1—C7	116.6 (2)	O1—C7—H7B	110.2
C2—C1—C6	121.0 (3)	C6—C7—H7B	110.2
C2—C1—H1A	119.5	H7A—C7—H7B	108.5
C6—C1—H1A	119.5	O1—C8—C13	115.5 (2)
C1—C2—C3	119.5 (3)	O1—C8—C9	124.9 (3)
C1—C2—H2A	120.2	C13—C8—C9	119.6 (3)
C3—C2—H2A	120.2	C10—C9—C8	119.2 (3)
C4—C3—C2	120.4 (3)	C10—C9—H9A	120.4
C4—C3—H3A	119.8	C8—C9—H9A	120.4
C2—C3—H3A	119.8	C9—C10—C11	122.1 (3)
C3—C4—C5	120.5 (3)	C9—C10—H10A	119.0
C3—C4—H4A	119.8	C11—C10—H10A	119.0
C5—C4—H4A	119.8	C10—C11—C12	116.9 (3)
C4—C5—C6	119.4 (3)	C10—C11—C14	122.1 (3)
C4—C5—H5A	120.3	C12—C11—C14	121.0 (3)
C6—C5—H5A	120.3	F1—C12—C13	119.4 (3)
C1—C6—C5	119.2 (3)	F1—C12—C11	117.5 (3)
C1—C6—C7	120.8 (3)	C13—C12—C11	123.0 (3)
C5—C6—C7	120.0 (3)	C12—C13—C8	119.2 (3)
O1—C7—C6	107.6 (2)	C12—C13—H13A	120.4
O1—C7—H7A	110.2	C8—C13—H13A	120.4
C6—C7—H7A	110.2	N1—C14—C11	178.9 (4)
C8—O1—C7—C6	−178.9 (2)	O1—C8—C13—C12	−178.4 (3)
C7—O1—C8—C13	−177.0 (2)	C9—C8—C13—C12	0.3 (4)
C7—O1—C8—C9	4.4 (4)	O1—C8—C9—C10	178.1 (3)
C6—C1—C2—C3	0.2 (5)	C13—C8—C9—C10	−0.5 (5)
C4—C3—C2—C1	−1.1 (5)	C8—C9—C10—C11	−0.7 (5)
C2—C3—C4—C5	1.5 (5)	C12—C11—C10—C9	2.0 (5)
C6—C5—C4—C3	−1.0 (5)	C14—C11—C10—C9	−179.4 (3)
C5—C6—C1—C2	0.3 (4)	F1—C12—C11—C10	177.0 (3)
C7—C6—C1—C2	−179.5 (3)	C13—C12—C11—C10	−2.3 (5)
C1—C6—C5—C4	0.1 (4)	F1—C12—C11—C14	−1.6 (5)
C7—C6—C5—C4	179.8 (3)	C13—C12—C11—C14	179.1 (3)
C1—C6—C7—O1	107.6 (3)	C8—C13—C12—F1	−178.1 (3)
C5—C6—C7—O1	−72.1 (3)	C8—C13—C12—C11	1.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg1^i	0.97	2.76	3.503	133

Symmetry code: (i) −x+1/2, −y−1/2, −z.