N'-(2,6-Difluoro-benzyl-idene)pyridine-4-carbohydrazide.

In the title compound, C(13)H(9)F(2)N(3)O, the pyridine ring forms a dihedral angle of 16.92 (7)° with the benzene ring. In the crystal, mol-ecules are linked via N-H⋯O, C-H⋯O and C-H⋯F, with the same O atom accepting two bonds.

Related literature

For related structures, see: Chen (2006 ▶); Nie et al. (2006 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H9F2N3O

M = 261.23

Monoclinic,

a = 6.8462 (1) Å

b = 24.7903 (5) Å

c = 8.3719 (1) Å

β = 125.249 (1)°

V = 1160.36 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.68 × 0.26 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.923, T max = 0.988

22044 measured reflections

4531 independent reflections

3819 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.117

S = 1.06

4531 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016716/bv2204sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016716/bv2204Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016716/bv2204Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H9F2N3O	F(000) = 536
Mr = 261.23	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8606 reflections
a = 6.8462 (1) Å	θ = 3.1–33.5°
b = 24.7903 (5) Å	µ = 0.12 mm−1
c = 8.3719 (1) Å	T = 100 K
β = 125.249 (1)°	Plate, colourless
V = 1160.36 (3) Å3	0.68 × 0.26 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4531 independent reflections
Radiation source: fine-focus sealed tube	3819 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 33.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.923, Tmax = 0.988	k = −38→38
22044 measured reflections	l = −12→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.3643P] where P = (Fo2 + 2Fc2)/3
4531 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
F1	0.41487 (12)	0.82429 (3)	−0.46332 (9)	0.02284 (14)
F2	0.74397 (12)	0.94647 (3)	0.06279 (9)	0.02428 (15)
O1	0.88240 (14)	0.69293 (3)	−0.10748 (11)	0.01802 (15)
N1	1.26302 (17)	0.60373 (4)	0.54592 (13)	0.02081 (18)
N2	0.85867 (15)	0.75837 (3)	0.07264 (12)	0.01533 (15)
N3	0.73916 (15)	0.79285 (3)	−0.08611 (12)	0.01499 (15)
C1	1.20146 (17)	0.69340 (4)	0.41379 (14)	0.01558 (17)
H1A	1.2365	0.7300	0.4362	0.019*
C2	1.30695 (18)	0.65690 (4)	0.56804 (15)	0.01889 (18)
H2A	1.4143	0.6701	0.6940	0.023*
C3	1.11063 (19)	0.58554 (4)	0.36284 (16)	0.01903 (19)
H3A	1.0787	0.5487	0.3448	0.023*
C4	0.99779 (17)	0.61841 (4)	0.19868 (15)	0.01578 (17)
H4A	0.8951	0.6039	0.0741	0.019*
C5	1.04182 (16)	0.67368 (4)	0.22471 (13)	0.01332 (16)
C6	0.92010 (16)	0.70905 (4)	0.04740 (14)	0.01366 (16)
C7	0.71196 (16)	0.84069 (4)	−0.04226 (14)	0.01461 (16)
H7A	0.7767	0.8489	0.0877	0.018*
C8	0.58232 (16)	0.88247 (4)	−0.19069 (14)	0.01341 (16)
C9	0.43387 (17)	0.87443 (4)	−0.39305 (14)	0.01554 (17)
C10	0.30493 (19)	0.91512 (4)	−0.52600 (15)	0.01971 (19)
H10A	0.2063	0.9079	−0.6594	0.024*
C11	0.3256 (2)	0.96720 (4)	−0.45622 (16)	0.0218 (2)
H11A	0.2382	0.9950	−0.5441	0.026*
C12	0.47472 (19)	0.97845 (4)	−0.25729 (16)	0.02061 (19)
H12A	0.4914	1.0134	−0.2107	0.025*
C13	0.59696 (17)	0.93600 (4)	−0.13148 (14)	0.01623 (17)
H1N2	0.870 (3)	0.7667 (7)	0.180 (3)	0.034 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0293 (3)	0.0157 (3)	0.0164 (3)	0.0010 (2)	0.0091 (3)	−0.0034 (2)
F2	0.0308 (3)	0.0188 (3)	0.0156 (3)	0.0007 (2)	0.0089 (3)	−0.0043 (2)
O1	0.0264 (4)	0.0163 (3)	0.0134 (3)	0.0014 (3)	0.0126 (3)	−0.0004 (2)
N1	0.0226 (4)	0.0217 (4)	0.0176 (4)	0.0037 (3)	0.0113 (3)	0.0052 (3)
N2	0.0211 (4)	0.0142 (3)	0.0117 (3)	0.0042 (3)	0.0100 (3)	0.0025 (3)
N3	0.0182 (3)	0.0143 (3)	0.0135 (3)	0.0027 (3)	0.0097 (3)	0.0029 (3)
C1	0.0165 (4)	0.0160 (4)	0.0139 (4)	0.0004 (3)	0.0086 (3)	−0.0003 (3)
C2	0.0183 (4)	0.0226 (4)	0.0133 (4)	0.0022 (3)	0.0077 (4)	0.0013 (3)
C3	0.0222 (4)	0.0154 (4)	0.0204 (5)	0.0021 (3)	0.0128 (4)	0.0037 (3)
C4	0.0175 (4)	0.0146 (4)	0.0158 (4)	0.0003 (3)	0.0100 (3)	0.0003 (3)
C5	0.0154 (4)	0.0135 (3)	0.0130 (4)	0.0014 (3)	0.0093 (3)	0.0011 (3)
C6	0.0154 (4)	0.0136 (3)	0.0127 (4)	0.0001 (3)	0.0085 (3)	0.0004 (3)
C7	0.0162 (4)	0.0149 (4)	0.0131 (4)	0.0010 (3)	0.0086 (3)	0.0009 (3)
C8	0.0155 (4)	0.0124 (3)	0.0138 (4)	0.0007 (3)	0.0093 (3)	0.0005 (3)
C9	0.0180 (4)	0.0139 (4)	0.0149 (4)	−0.0001 (3)	0.0096 (3)	−0.0009 (3)
C10	0.0225 (4)	0.0199 (4)	0.0143 (4)	0.0025 (3)	0.0092 (4)	0.0032 (3)
C11	0.0269 (5)	0.0168 (4)	0.0210 (5)	0.0048 (3)	0.0135 (4)	0.0061 (4)
C12	0.0266 (5)	0.0135 (4)	0.0224 (5)	0.0020 (3)	0.0146 (4)	0.0015 (3)
C13	0.0192 (4)	0.0146 (4)	0.0150 (4)	−0.0003 (3)	0.0099 (3)	−0.0012 (3)

F1—C9	1.3488 (11)	C4—C5	1.3928 (13)
F2—C13	1.3550 (12)	C4—H4A	0.9300
O1—C6	1.2334 (11)	C5—C6	1.4963 (13)
N1—C3	1.3399 (14)	C7—C8	1.4601 (13)
N1—C2	1.3410 (14)	C7—H7A	0.9300
N2—C6	1.3485 (12)	C8—C9	1.3983 (13)
N2—N3	1.3826 (11)	C8—C13	1.3998 (13)
N2—H1N2	0.884 (18)	C9—C10	1.3790 (14)
N3—C7	1.2864 (12)	C10—C11	1.3901 (15)
C1—C2	1.3897 (14)	C10—H10A	0.9300
C1—C5	1.3936 (13)	C11—C12	1.3897 (16)
C1—H1A	0.9300	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.3783 (14)
C3—C4	1.3872 (14)	C12—H12A	0.9300
C3—H3A	0.9300
C3—N1—C2	116.95 (9)	N2—C6—C5	114.91 (8)
C6—N2—N3	118.36 (8)	N3—C7—C8	121.88 (9)
C6—N2—H1N2	121.3 (11)	N3—C7—H7A	119.1
N3—N2—H1N2	119.4 (11)	C8—C7—H7A	119.1
C7—N3—N2	113.49 (8)	C9—C8—C13	114.68 (8)
C2—C1—C5	118.26 (9)	C9—C8—C7	126.14 (8)
C2—C1—H1A	120.9	C13—C8—C7	119.14 (9)
C5—C1—H1A	120.9	F1—C9—C10	117.80 (9)
N1—C2—C1	123.84 (9)	F1—C9—C8	118.65 (8)
N1—C2—H2A	118.1	C10—C9—C8	123.55 (9)
C1—C2—H2A	118.1	C9—C10—C11	118.53 (10)
N1—C3—C4	123.81 (9)	C9—C10—H10A	120.7
N1—C3—H3A	118.1	C11—C10—H10A	120.7
C4—C3—H3A	118.1	C12—C11—C10	121.09 (9)
C3—C4—C5	118.45 (9)	C12—C11—H11A	119.5
C3—C4—H4A	120.8	C10—C11—H11A	119.5
C5—C4—H4A	120.8	C13—C12—C11	117.68 (9)
C4—C5—C1	118.67 (9)	C13—C12—H12A	121.2
C4—C5—C6	118.35 (8)	C11—C12—H12A	121.2
C1—C5—C6	122.96 (8)	F2—C13—C12	118.28 (9)
O1—C6—N2	124.30 (9)	F2—C13—C8	117.29 (8)
O1—C6—C5	120.79 (8)	C12—C13—C8	124.43 (9)
C6—N2—N3—C7	−172.82 (9)	N3—C7—C8—C9	14.15 (15)
C3—N1—C2—C1	1.03 (16)	N3—C7—C8—C13	−167.93 (9)
C5—C1—C2—N1	−0.46 (15)	C13—C8—C9—F1	178.07 (8)
C2—N1—C3—C4	−0.28 (16)	C7—C8—C9—F1	−3.93 (15)
N1—C3—C4—C5	−0.99 (15)	C13—C8—C9—C10	−1.87 (14)
C3—C4—C5—C1	1.52 (14)	C7—C8—C9—C10	176.13 (10)
C3—C4—C5—C6	179.93 (9)	F1—C9—C10—C11	−178.93 (9)
C2—C1—C5—C4	−0.85 (14)	C8—C9—C10—C11	1.00 (16)
C2—C1—C5—C6	−179.18 (9)	C9—C10—C11—C12	0.75 (17)
N3—N2—C6—O1	2.02 (14)	C10—C11—C12—C13	−1.46 (17)
N3—N2—C6—C5	−178.14 (8)	C11—C12—C13—F2	179.64 (9)
C4—C5—C6—O1	−34.71 (13)	C11—C12—C13—C8	0.49 (16)
C1—C5—C6—O1	143.63 (10)	C9—C8—C13—F2	−178.05 (9)
C4—C5—C6—N2	145.45 (9)	C7—C8—C13—F2	3.79 (13)
C1—C5—C6—N2	−36.22 (13)	C9—C8—C13—C12	1.10 (15)
N2—N3—C7—C8	−177.64 (8)	C7—C8—C13—C12	−177.05 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.88 (2)	2.00 (2)	2.8554 (12)	163.4 (16)
C1—H1A···F1ii	0.93	2.54	3.4622 (13)	169
C7—H7A···O1i	0.93	2.45	3.2253 (13)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.88 (2)	2.00 (2)	2.8554 (12)	163.4 (16)
C1—H1A⋯F1ii	0.93	2.54	3.4622 (13)	169
C7—H7A⋯O1i	0.93	2.45	3.2253 (13)	141

Symmetry codes: (i) ; (ii) .