Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C6H5FN2O, exists as the E isomer. The crystal structure is stabilized by O—H...N hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032533/xu2070sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032533/xu2070Isup2.hkl
Contains datablock I

CCDC reference: 621539

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

Computing details top

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 top
Crystal data top
C6H5FN2OF(000) = 288
Mr = 140.12Dx = 1.474 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 252 reflections
a = 8.006 (2) Åθ = 2.5–20.7°
b = 8.525 (2) ŵ = 0.12 mm1
c = 9.260 (2) ÅT = 293 K
β = 91.998 (5)°Prism, colorless
V = 631.6 (3) Å30.13 × 0.11 × 0.07 mm
Z = 4
Data collection top
Bruker SMART APEX CCD detector
diffractometer
582 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.067
Graphite monochromatorθmax = 26.0°, θmin = 2.5°
φ and ω scansh = 98
3566 measured reflectionsk = 1010
1250 independent reflectionsl = 911
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0465P)2]
where P = (Fo2 + 2Fc2)/3
1250 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.24 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.8952 (2)0.0145 (2)1.1302 (2)0.0716 (8)
N10.7137 (3)0.1128 (3)0.9842 (3)0.0416 (7)
N20.4620 (3)0.3511 (3)0.7545 (3)0.0434 (8)
O10.3320 (3)0.3151 (2)0.6552 (2)0.0547 (7)
H10.32000.41370.58890.082*
C10.8359 (4)0.1257 (4)1.0818 (4)0.0466 (9)
C20.9038 (4)0.2605 (5)1.1368 (4)0.0578 (11)
H20.99100.25941.20580.069*
C30.8366 (4)0.3973 (4)1.0848 (4)0.0543 (10)
H30.87800.49301.11830.065*
C40.7067 (4)0.3932 (4)0.9821 (3)0.0473 (9)
H40.65960.48560.94620.057*
C50.6486 (4)0.2495 (4)0.9340 (3)0.0384 (8)
C60.5128 (4)0.2321 (4)0.8239 (3)0.0434 (9)
H60.46500.13440.80570.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0807 (16)0.0614 (15)0.0706 (16)0.0172 (12)0.0283 (12)0.0082 (12)
N10.0436 (18)0.0417 (17)0.0390 (17)0.0035 (14)0.0058 (14)0.0006 (14)
N20.0445 (18)0.0408 (16)0.0443 (17)0.0014 (15)0.0082 (14)0.0013 (14)
O10.0574 (16)0.0473 (15)0.0576 (16)0.0001 (12)0.0247 (13)0.0069 (12)
C10.047 (2)0.047 (2)0.045 (2)0.0081 (18)0.0034 (19)0.0007 (19)
C20.049 (2)0.068 (3)0.055 (3)0.003 (2)0.015 (2)0.013 (2)
C30.057 (3)0.048 (2)0.057 (3)0.0066 (19)0.006 (2)0.013 (2)
C40.051 (2)0.042 (2)0.049 (2)0.0017 (18)0.0002 (19)0.0036 (18)
C50.0392 (19)0.0355 (18)0.040 (2)0.0022 (17)0.0017 (16)0.0011 (18)
C60.044 (2)0.0362 (19)0.049 (2)0.0032 (17)0.0080 (18)0.0019 (18)
Geometric parameters (Å, º) top
F1—C11.356 (3)C2—H20.9300
N1—C11.313 (4)C3—C41.385 (4)
N1—C51.353 (4)C3—H30.9300
N2—C61.260 (3)C4—C51.379 (4)
N2—O11.399 (3)C4—H40.9300
O1—H11.0429C5—C61.472 (4)
C1—C21.363 (5)C6—H60.9300
C2—C31.365 (5)
C1—N1—C5115.7 (3)C4—C3—H3120.1
C6—N2—O1112.2 (2)C5—C4—C3118.7 (3)
N2—O1—H1105.2C5—C4—H4120.6
N1—C1—F1113.4 (3)C3—C4—H4120.6
N1—C1—C2127.3 (3)N1—C5—C4122.2 (3)
F1—C1—C2119.3 (3)N1—C5—C6114.7 (3)
C1—C2—C3116.2 (3)C4—C5—C6123.1 (3)
C1—C2—H2121.9N2—C6—C5119.3 (3)
C3—C2—H2121.9N2—C6—H6120.3
C2—C3—C4119.9 (3)C5—C6—H6120.3
C2—C3—H3120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i1.041.842.865 (3)165
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds