Pyridine-3-carbaldehyde 2-pyridylhydrazone

In the crystal structure of the title compound, C₁₁H₁₀N₄, mol­ecules form dimers , which form a zigzag pattern in the crystal. The hydrogen-bond network can be described by graph-set notation as R₂²(14).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.047
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ...       1.19
PLAT411_ALERT_2_B Short Inter H...H Contact  H1     ..  H11     ..       2.06 Ang.

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.660
            Test value =      0.525
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.66 e/A   
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....         H1
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....         H2
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....         H3
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....         H4
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....         H5
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....         H6
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....         H8
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....         H9
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H10
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H11
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       5.63 su
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N2     -   H2     ...       1.03 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
   2 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

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

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S1. Comment

2-Pyridylhydrazone (2-pyridinylhydrazone 3-Pyridinecarboxaldehyde, I) belongs to the class of heterocyclic hydrazones, which have an anti-tuberculosis activity (Cory et al., 1994; Seydel et al., 1994). These compounds show some inhibitory activity towards ribonucleotide reductase and anticonvulsant activity as well (Popp, 1989). Crystal structure of (I) has not been solved before. Therefore the aim of the work was to fill this gap. A view of molecule (I) with the atomic numbering is presented in Fig 1. The parameters of the hydrogen bond geometry are shown in Table 1. The bond lengths are within the normal range of such bonds (Allen et al., 1987). The conformational state of the molecule in the crystal structure can be characterized in the following way. The torsion angle N1—C1—C2—C3, which characterizes the orientation of the one pyridine fragment Py1 [N4—C6–C2—C3—C4—C5] with respect to bridge group (C1—N1—N2), is 3.5 (2) °. At other side, he torsion angle C8—C7—N2—N1, which describes the orientation of the second pyridine ring Py2 [N3—C7–C8—C9—C10—C11] with respect to the bridge group, is 0.9 (2) °. The torsion angle C2–C1—N1—N2, which characterize a planarity of bridge group, is 178.86 (13) °. The pyridine fragments are rotated relatively o each other by 8.2 (2)°. The molecular packing architecture is shown in Figs. 2 & 3. The molecules of (I) form dimers by hydrogen bonds N2—H2···N3. The hydrogen-bond network can be described by the graph-set assignment introduced by Etter (1990) as R₂²(14). The dimers are packed in cups where interact to each other by van-der-Waals forces.

Related literature

For related literature, see: Allen et al. (1987); Cory et al. (1994); Etter (1990); Popp (1989); Seydel et al. (1994).

S2. Experimental

The chemical synthesis of the title compound was performed by analogy to procedures described previously (Popp, 1989). Generally, the compound was recrystallized from methanol/water. The 2-Pyridylhydrazone crystal was grown by slow evaporation from methanol solution.

Computing details

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SIR88 (Burla et al., 1989 Reference OK?); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); software used to prepare material for publication: CrystalStructure.

Figures

	Fig. 1. A view of I with the atomic numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. Projection of crystal lattice molecular packing of (I) along OX axis.
	Fig. 3. Projection of crystal lattice molecular packing of (I) along OY axis.

Pyridine-3-carbaldehyde 2-pyridylhydrazone

Crystal data

C11H10N4	F(000) = 416.00
Mr = 198.23	Dx = 1.325 Mg m^−3
Monoclinic, P21/n	Melting point: 449 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71070 Å
a = 10.896 (5) Å	Cell parameters from 1851 reflections
b = 4.0270 (17) Å	θ = 3.2–30.0°
c = 22.710 (9) Å	µ = 0.09 mm^−1
β = 94.304 (8)°	T = 293 K
V = 993.6 (7) Å^3	Prism, colorless
Z = 4	0.40 × 0.30 × 0.10 mm

Data collection

Rigaku Saturn diffractometer	2273 reflections with F^2 > 2σ(F^2)
Detector resolution: 7.31 pixels mm^-1	Rint = 0.037
ω scans	θmax = 30.4°
Absorption correction: multi-scan Jacobson (1998)	h = −14→14
Tmin = 0.892, Tmax = 0.992	k = −3→5
9025 measured reflections	l = −32→31
3614 independent reflections

Refinement

Refinement on F	Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 88.1628 106.9210 44.1569
R[F^2 > 2σ(F^2)] = 0.045	(Δ/σ)max = 0.006
wR(F^2) = 0.048	Δρmax = 0.66 e Å^−3
S = 0.97	Δρmin = −0.52 e Å^−3
3614 reflections	Extinction correction: Larson (1970) Crystallographic Computing eq. 22
177 parameters	Extinction coefficient: 41 (21)
All H-atom parameters refined

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 3.0 σ(F²). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
N1	0.58600 (12)	0.1829 (3)	0.62487 (5)	0.0552 (4)
N2	0.57422 (12)	0.2776 (3)	0.56706 (5)	0.0583 (4)
N3	0.64083 (11)	0.2790 (3)	0.47412 (5)	0.0573 (4)
N4	0.39775 (16)	0.1814 (4)	0.80823 (6)	0.0817 (6)
C1	0.49701 (17)	0.2595 (4)	0.65614 (6)	0.0565 (5)
C2	0.50216 (14)	0.1730 (4)	0.71847 (6)	0.0508 (5)
C3	0.60286 (18)	0.0237 (4)	0.74843 (6)	0.0572 (5)
C4	0.6002 (2)	−0.0391 (4)	0.80754 (8)	0.0679 (6)
C5	0.4975 (2)	0.0415 (5)	0.83536 (9)	0.0752 (7)
C6	0.40282 (18)	0.2461 (5)	0.75060 (8)	0.0685 (6)
C7	0.66146 (14)	0.1757 (4)	0.53006 (6)	0.0501 (5)
C8	0.76185 (16)	−0.0184 (4)	0.54956 (8)	0.0579 (5)
C9	0.84375 (19)	−0.1077 (4)	0.50947 (9)	0.0680 (6)
C10	0.82507 (18)	−0.0028 (4)	0.45175 (8)	0.0669 (6)
C11	0.72443 (17)	0.1861 (4)	0.43666 (8)	0.0614 (6)
H1	0.4229 (13)	0.386 (3)	0.6392 (5)	0.059 (4)*
H2	0.4999 (17)	0.419 (4)	0.5523 (7)	0.101 (6)*
H3	0.6766 (12)	−0.036 (3)	0.7269 (5)	0.058 (4)*
H4	0.6726 (14)	−0.133 (4)	0.8288 (6)	0.075 (5)*
H5	0.4973 (14)	0.002 (4)	0.8809 (7)	0.092 (5)*
H6	0.3308 (14)	0.349 (3)	0.7279 (6)	0.078 (5)*
H8	0.7715 (12)	−0.100 (3)	0.5907 (6)	0.061 (4)*
H9	0.9192 (14)	−0.251 (4)	0.5233 (6)	0.078 (5)*
H10	0.8840 (13)	−0.067 (3)	0.4231 (6)	0.069 (4)*
H11	0.7058 (13)	0.271 (3)	0.3930 (6)	0.071 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0598 (9)	0.0669 (10)	0.0390 (7)	−0.0061 (7)	0.0043 (6)	0.0036 (6)
N2	0.0522 (9)	0.0841 (11)	0.0390 (7)	0.0041 (8)	0.0049 (7)	0.0107 (7)
N3	0.0558 (8)	0.0752 (10)	0.0411 (7)	−0.0023 (7)	0.0056 (6)	0.0025 (7)
N4	0.0849 (12)	0.1059 (13)	0.0575 (10)	−0.0055 (10)	0.0267 (9)	0.0024 (9)
C1	0.0503 (11)	0.0746 (14)	0.0447 (10)	0.0025 (10)	0.0046 (8)	0.0070 (9)
C2	0.0500 (10)	0.0583 (11)	0.0445 (8)	−0.0014 (8)	0.0070 (8)	0.0002 (8)
C3	0.0602 (11)	0.0648 (12)	0.0472 (10)	−0.0018 (10)	0.0072 (9)	0.0035 (9)
C4	0.0756 (14)	0.0746 (13)	0.0529 (12)	−0.0008 (11)	−0.0003 (11)	0.0077 (10)
C5	0.0966 (17)	0.0823 (15)	0.0478 (11)	−0.0209 (13)	0.0121 (12)	0.0046 (11)
C6	0.0600 (12)	0.0914 (16)	0.0552 (11)	0.0032 (11)	0.0129 (10)	0.0052 (11)
C7	0.0486 (10)	0.0576 (11)	0.0445 (9)	−0.0085 (9)	0.0056 (8)	−0.0009 (8)
C8	0.0608 (12)	0.0626 (12)	0.0499 (10)	−0.0022 (9)	0.0026 (9)	0.0042 (10)
C9	0.0669 (13)	0.0690 (14)	0.0688 (13)	0.0071 (10)	0.0104 (10)	0.0033 (10)
C10	0.0723 (14)	0.0683 (13)	0.0626 (11)	0.0054 (11)	0.0224 (10)	−0.0035 (10)
C11	0.0668 (12)	0.0700 (13)	0.0483 (10)	−0.0022 (10)	0.0107 (9)	−0.0009 (9)

Geometric parameters (Å, º)

N1—N2	1.3640 (16)	C8—C9	1.370 (2)
N1—C1	1.282 (2)	C9—C10	1.378 (2)
N2—C7	1.378 (2)	C10—C11	1.357 (2)
N3—C7	1.3396 (19)	N2—H2	1.026 (18)
N3—C11	1.345 (2)	C1—H1	1.007 (14)
N4—C5	1.334 (2)	C3—H3	1.001 (14)
N4—C6	1.340 (2)	C4—H4	0.971 (15)
C1—C2	1.455 (2)	C5—H5	1.048 (17)
C2—C3	1.384 (2)	C6—H6	0.996 (15)
C2—C6	1.382 (2)	C8—H8	0.988 (14)
C3—C4	1.368 (2)	C9—H9	1.034 (16)
C4—C5	1.364 (3)	C10—H10	0.981 (15)
C7—C8	1.390 (2)	C11—H11	1.054 (14)
N2—N1—C1	116.45 (13)	C7—N2—H2	122.0 (9)
N1—N2—C7	118.97 (13)	N1—C1—H1	122.0 (8)
C7—N3—C11	116.11 (13)	C2—C1—H1	117.6 (8)
C5—N4—C6	116.20 (18)	C2—C3—H3	120.0 (7)
N1—C1—C2	120.39 (15)	C4—C3—H3	120.8 (7)
C1—C2—C3	123.61 (15)	C3—C4—H4	118.9 (9)
C1—C2—C6	119.24 (15)	C5—C4—H4	121.8 (9)
C3—C2—C6	117.15 (15)	N4—C5—H5	117.3 (8)
C2—C3—C4	119.20 (17)	C4—C5—H5	119.0 (8)
C3—C4—C5	119.28 (19)	N4—C6—H6	119.8 (9)
N4—C5—C4	123.69 (18)	C2—C6—H6	115.7 (9)
N4—C6—C2	124.47 (17)	C7—C8—H8	120.8 (8)
N2—C7—N3	114.31 (13)	C9—C8—H8	120.9 (8)
N2—C7—C8	122.40 (14)	C8—C9—H9	119.2 (8)
N3—C7—C8	123.29 (15)	C10—C9—H9	121.1 (8)
C7—C8—C9	118.19 (16)	C9—C10—H10	119.5 (8)
C8—C9—C10	119.65 (18)	C11—C10—H10	122.4 (8)
C9—C10—C11	118.10 (18)	N3—C11—H11	114.5 (8)
N3—C11—C10	124.66 (16)	C10—C11—H11	120.9 (8)
N1—N2—H2	119.0 (9)
N2—N1—C1—C2	−179.10 (14)	C1—C2—C3—C4	178.10 (17)
C1—N1—N2—C7	−174.09 (15)	C1—C2—C6—N4	−179.27 (17)
N1—N2—C7—N3	179.33 (13)	C3—C2—C6—N4	−0.2 (2)
N1—N2—C7—C8	−0.5 (2)	C6—C2—C3—C4	−1.0 (2)
C7—N3—C11—C10	0.5 (2)	C2—C3—C4—C5	1.2 (2)
C11—N3—C7—N2	179.64 (14)	C3—C4—C5—N4	−0.2 (3)
C11—N3—C7—C8	−0.5 (2)	N2—C7—C8—C9	179.95 (14)
C5—N4—C6—C2	1.1 (2)	N3—C7—C8—C9	0.1 (2)
C6—N4—C5—C4	−0.8 (3)	C7—C8—C9—C10	0.4 (2)
N1—C1—C2—C3	3.7 (2)	C8—C9—C10—C11	−0.4 (2)
N1—C1—C2—C6	−177.31 (16)	C9—C10—C11—N3	−0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3^i	1.026 (18)	2.012 (18)	3.0371 (18)	176.5 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.