(E)-6-Fluoro­pyridine-2-carbaldehyde oxime

The title compound, C₆H₅FN₂O, exists as the E isomer. The crystal structure is stabilized by O—H...N hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.061
• wR factor = 0.135
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1     -   H1     ...       1.04 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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 (Bruker, 1998); cell refinement: SAINT (Bruker, 2003); 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.

(E)-6-fluoropyridine-2-carbaldehyde oxime

Crystal data

C6H5FN2O	F(000) = 288
Mr = 140.12	Dx = 1.474 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 252 reflections
a = 8.006 (2) Å	θ = 2.5–20.7°
b = 8.525 (2) Å	µ = 0.12 mm^−1
c = 9.260 (2) Å	T = 293 K
β = 91.998 (5)°	Prism, colorless
V = 631.6 (3) Å^3	0.13 × 0.11 × 0.07 mm
Z = 4

Data collection

Bruker SMART APEX CCD detector diffractometer	582 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
Graphite monochromator	θmax = 26.0°, θmin = 2.5°
φ and ω scans	h = −9→8
3566 measured reflections	k = −10→10
1250 independent reflections	l = −9→11

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0465P)^2] where P = (Fo^2 + 2Fc^2)/3
1250 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.24 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.8952 (2)	−0.0145 (2)	1.1302 (2)	0.0716 (8)
N1	0.7137 (3)	0.1128 (3)	0.9842 (3)	0.0416 (7)
N2	0.4620 (3)	0.3511 (3)	0.7545 (3)	0.0434 (8)
O1	0.3320 (3)	0.3151 (2)	0.6552 (2)	0.0547 (7)
H1	0.3200	0.4137	0.5889	0.082*
C1	0.8359 (4)	0.1257 (4)	1.0818 (4)	0.0466 (9)
C2	0.9038 (4)	0.2605 (5)	1.1368 (4)	0.0578 (11)
H2	0.9910	0.2594	1.2058	0.069*
C3	0.8366 (4)	0.3973 (4)	1.0848 (4)	0.0543 (10)
H3	0.8780	0.4930	1.1183	0.065*
C4	0.7067 (4)	0.3932 (4)	0.9821 (3)	0.0473 (9)
H4	0.6596	0.4856	0.9462	0.057*
C5	0.6486 (4)	0.2495 (4)	0.9340 (3)	0.0384 (8)
C6	0.5128 (4)	0.2321 (4)	0.8239 (3)	0.0434 (9)
H6	0.4650	0.1344	0.8057	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0807 (16)	0.0614 (15)	0.0706 (16)	0.0172 (12)	−0.0283 (12)	0.0082 (12)
N1	0.0436 (18)	0.0417 (17)	0.0390 (17)	0.0035 (14)	−0.0058 (14)	−0.0006 (14)
N2	0.0445 (18)	0.0408 (16)	0.0443 (17)	0.0014 (15)	−0.0082 (14)	0.0013 (14)
O1	0.0574 (16)	0.0473 (15)	0.0576 (16)	0.0001 (12)	−0.0247 (13)	0.0069 (12)
C1	0.047 (2)	0.047 (2)	0.045 (2)	0.0081 (18)	−0.0034 (19)	−0.0007 (19)
C2	0.049 (2)	0.068 (3)	0.055 (3)	−0.003 (2)	−0.015 (2)	−0.013 (2)
C3	0.057 (3)	0.048 (2)	0.057 (3)	−0.0066 (19)	−0.006 (2)	−0.013 (2)
C4	0.051 (2)	0.042 (2)	0.049 (2)	0.0017 (18)	−0.0002 (19)	−0.0036 (18)
C5	0.0392 (19)	0.0355 (18)	0.040 (2)	−0.0022 (17)	−0.0017 (16)	−0.0011 (18)
C6	0.044 (2)	0.0362 (19)	0.049 (2)	−0.0032 (17)	−0.0080 (18)	−0.0019 (18)

Geometric parameters (Å, º)

F1—C1	1.356 (3)	C2—H2	0.9300
N1—C1	1.313 (4)	C3—C4	1.385 (4)
N1—C5	1.353 (4)	C3—H3	0.9300
N2—C6	1.260 (3)	C4—C5	1.379 (4)
N2—O1	1.399 (3)	C4—H4	0.9300
O1—H1	1.0429	C5—C6	1.472 (4)
C1—C2	1.363 (5)	C6—H6	0.9300
C2—C3	1.365 (5)
C1—N1—C5	115.7 (3)	C4—C3—H3	120.1
C6—N2—O1	112.2 (2)	C5—C4—C3	118.7 (3)
N2—O1—H1	105.2	C5—C4—H4	120.6
N1—C1—F1	113.4 (3)	C3—C4—H4	120.6
N1—C1—C2	127.3 (3)	N1—C5—C4	122.2 (3)
F1—C1—C2	119.3 (3)	N1—C5—C6	114.7 (3)
C1—C2—C3	116.2 (3)	C4—C5—C6	123.1 (3)
C1—C2—H2	121.9	N2—C6—C5	119.3 (3)
C3—C2—H2	121.9	N2—C6—H6	120.3
C2—C3—C4	119.9 (3)	C5—C6—H6	120.3
C2—C3—H3	120.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^i	1.04	1.84	2.865 (3)	165

Symmetry code: (i) −x+1, y+1/2, −z+3/2.