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The molecule of the title compound, 4-fluoro­benz­aldehyde (pyridine-2-carbonyl)­hydrazone, C13H10FN3O, is roughly planar and displays a trans configuration with respect to the C=N double bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027369/cf6386sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027369/cf6386Isup2.hkl
Contains datablock I

CCDC reference: 259094

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.054
  • wR factor = 0.145
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C4 PLAT731_ALERT_1_C Bond Calc 0.888(19), Rep 0.890(9) ...... 2.11 su-Rat N2 -H2A 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

4-fluorobenzaldehyde (pyridine-2-carbonyl)hydrazone top
Crystal data top
C13H10FN3OF(000) = 504
Mr = 243.24Dx = 1.418 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1485 reflections
a = 5.812 (3) Åθ = 2.9–23.5°
b = 14.276 (8) ŵ = 0.11 mm1
c = 13.878 (7) ÅT = 298 K
β = 98.344 (8)°Block, yellow
V = 1139.3 (11) Å30.38 × 0.28 × 0.23 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2342 independent reflections
Radiation source: fine-focus sealed tube1493 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.961, Tmax = 0.976k = 1417
6467 measured reflectionsl = 1717
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0611P)2 + 0.1645P]
where P = (Fo2 + 2Fc2)/3
2342 reflections(Δ/σ)max < 0.001
166 parametersΔρmax = 0.14 e Å3
1 restraintΔρmin = 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.

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 (Å2) top
xyzUiso*/Ueq
F10.4242 (3)0.40730 (8)0.09523 (11)0.0990 (5)
O10.2861 (3)0.11441 (10)0.17249 (12)0.0771 (5)
N10.0871 (3)0.01069 (11)0.13181 (12)0.0555 (5)
N20.0771 (3)0.10717 (11)0.13213 (13)0.0581 (5)
N30.0927 (3)0.29199 (11)0.11314 (13)0.0585 (5)
C10.3131 (3)0.12462 (13)0.10861 (13)0.0486 (5)
C20.1561 (4)0.18755 (14)0.13710 (15)0.0592 (6)
H20.02260.16540.15910.071*
C30.1933 (4)0.28261 (14)0.13352 (17)0.0686 (6)
H30.08780.32470.15360.082*
C40.3884 (4)0.31328 (14)0.09992 (16)0.0638 (6)
C50.5470 (4)0.25455 (16)0.07090 (16)0.0723 (7)
H50.67830.27760.04770.087*
C60.5093 (4)0.15937 (15)0.07656 (15)0.0651 (6)
H60.61870.11790.05830.078*
C70.2759 (4)0.02381 (13)0.11254 (14)0.0547 (5)
H70.39440.01640.10050.066*
C80.1143 (4)0.15235 (13)0.15109 (14)0.0532 (5)
C90.0953 (3)0.25730 (12)0.14492 (13)0.0479 (5)
C100.2673 (4)0.31186 (14)0.17242 (15)0.0623 (6)
H100.39740.28460.19270.075*
C110.2453 (4)0.40805 (15)0.16965 (17)0.0720 (7)
H110.35760.44690.18980.086*
C120.0557 (4)0.44434 (14)0.13674 (17)0.0696 (7)
H120.03610.50890.13340.084*
C130.1058 (4)0.38492 (14)0.10853 (17)0.0694 (6)
H130.23280.41100.08460.083*
H2A0.194 (3)0.1409 (14)0.1159 (15)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1118 (13)0.0452 (8)0.1345 (12)0.0202 (7)0.0010 (10)0.0133 (7)
O10.0698 (11)0.0487 (9)0.1167 (13)0.0147 (8)0.0270 (9)0.0043 (8)
N10.0650 (12)0.0316 (9)0.0702 (11)0.0032 (8)0.0110 (9)0.0012 (7)
N20.0635 (12)0.0311 (9)0.0817 (12)0.0080 (8)0.0174 (9)0.0006 (8)
N30.0587 (11)0.0371 (9)0.0817 (12)0.0033 (7)0.0169 (9)0.0038 (8)
C10.0517 (12)0.0397 (10)0.0542 (11)0.0007 (9)0.0069 (9)0.0034 (8)
C20.0559 (13)0.0425 (11)0.0809 (14)0.0007 (9)0.0160 (11)0.0002 (10)
C30.0702 (16)0.0392 (12)0.0962 (17)0.0061 (10)0.0114 (13)0.0001 (10)
C40.0738 (16)0.0405 (12)0.0733 (14)0.0099 (11)0.0026 (12)0.0068 (10)
C50.0695 (17)0.0674 (15)0.0819 (16)0.0213 (12)0.0177 (13)0.0045 (12)
C60.0600 (14)0.0590 (14)0.0785 (15)0.0005 (11)0.0178 (12)0.0084 (11)
C70.0557 (13)0.0414 (11)0.0674 (13)0.0090 (9)0.0102 (10)0.0043 (9)
C80.0590 (13)0.0395 (11)0.0608 (12)0.0067 (9)0.0079 (10)0.0006 (9)
C90.0531 (13)0.0373 (10)0.0527 (11)0.0040 (8)0.0062 (9)0.0004 (8)
C100.0610 (14)0.0498 (12)0.0786 (14)0.0007 (10)0.0186 (11)0.0004 (10)
C110.0730 (17)0.0494 (13)0.0949 (17)0.0113 (11)0.0160 (14)0.0061 (11)
C120.0781 (17)0.0331 (11)0.0959 (17)0.0010 (11)0.0070 (13)0.0035 (11)
C130.0675 (15)0.0429 (12)0.0999 (17)0.0079 (11)0.0185 (13)0.0074 (11)
Geometric parameters (Å, º) top
F1—C41.361 (2)C4—C51.350 (3)
O1—C81.210 (2)C5—C61.381 (3)
N1—C71.266 (3)C5—H50.9300
N1—N21.379 (2)C6—H60.9300
N2—C81.345 (3)C7—H70.9300
N2—H2A0.890 (9)C8—C91.506 (3)
N3—C131.331 (3)C9—C101.365 (3)
N3—C91.332 (2)C10—C111.380 (3)
C1—C61.375 (3)C10—H100.9300
C1—C21.379 (3)C11—C121.355 (3)
C1—C71.458 (3)C11—H110.9300
C2—C31.376 (3)C12—C131.364 (3)
C2—H20.9300C12—H120.9300
C3—C41.359 (3)C13—H130.9300
C3—H30.9300
C7—N1—N2115.32 (17)C5—C6—H6119.3
C8—N2—N1121.09 (17)N1—C7—C1122.00 (18)
C8—N2—H2A118.4 (15)N1—C7—H7119.0
N1—N2—H2A120.4 (15)C1—C7—H7119.0
C13—N3—C9116.22 (18)O1—C8—N2124.66 (19)
C6—C1—C2118.16 (19)O1—C8—C9121.98 (19)
C6—C1—C7120.19 (18)N2—C8—C9113.35 (17)
C2—C1—C7121.65 (18)N3—C9—C10123.36 (18)
C3—C2—C1121.2 (2)N3—C9—C8117.36 (17)
C3—C2—H2119.4C10—C9—C8119.28 (18)
C1—C2—H2119.4C9—C10—C11119.1 (2)
C4—C3—C2118.3 (2)C9—C10—H10120.5
C4—C3—H3120.9C11—C10—H10120.5
C2—C3—H3120.9C12—C11—C10118.2 (2)
C5—C4—C3122.8 (2)C12—C11—H11120.9
C5—C4—F1118.8 (2)C10—C11—H11120.9
C3—C4—F1118.4 (2)C11—C12—C13119.1 (2)
C4—C5—C6118.2 (2)C11—C12—H12120.5
C4—C5—H5120.9C13—C12—H12120.5
C6—C5—H5120.9N3—C13—C12124.0 (2)
C1—C6—C5121.3 (2)N3—C13—H13118.0
C1—C6—H6119.3C12—C13—H13118.0
 

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