Synthesis and characterization of (6-{[2-(pyridin-2-yl)hydrazinyl­idene]meth­yl}pyridin-2-yl)methanol: a supra­molecular and topological study

Hydrazones exhibit a versatile chemistry and are of inter­est for their potential use as functional mol­ecular systems capable of undergoing reversible changes of configuration, i.e. E/Z isomerization. The title compound, C₁₂H₁₂N₄O, has an E configuration with respect to the hydrazone C=N bond. The crystal packing is formed by N—H...N and O—H...N hydrogen bonds that give a two-dimensional layer structure and C—H...C inter­actions associated with layer stacking to produce the three-dimensional supra­molecular structure. These inter­molecular inter­actions were analyzed and qu­anti­fied by the Hirshfeld surface method and the two-dimensional supra­molecular arrangement was topologically simplified as a hcb network.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2008), TOPOS (Blatov et al., 2014) and CrystalExplorer (McKinnon et al., 2004); software used to prepare material for publication: WinGX (Farrugia, 2012).

(6-{[2-(Pyridin-2-yl)hydrazinylidene]methyl}pyridin-2-yl)methanol

Crystal data

C12H12N4O	F(000) = 960
Mr = 228.26	Dx = 1.362 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.461 (5) Å	Cell parameters from 2000 reflections
b = 5.5965 (13) Å	θ = 2.9–26.4°
c = 17.068 (3) Å	µ = 0.09 mm^−1
β = 96.544 (13)°	T = 291 K
V = 2226.4 (8) Å^3	Needle, yellow
Z = 8	0.2 × 0.1 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer	Rint = 0.134
CCD rotation images, thick slices scans	θmax = 26.4°, θmin = 3.1°
21975 measured reflections	h = −28→28
2255 independent reflections	k = −6→6
1116 reflections with I > 2σ(I)	l = −21→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0585P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.83	(Δ/σ)max < 0.001
2250 reflections	Δρmax = 0.16 e Å^−3
156 parameters	Δρmin = −0.14 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
C1	0.24078 (7)	−0.1570 (3)	0.81410 (11)	0.0639 (5)
H1A	0.2627	−0.1388	0.7696	0.077*
H1B	0.2406	−0.0037	0.8406	0.077*
C2	0.17994 (7)	−0.2219 (3)	0.78368 (10)	0.0517 (5)
C3	0.15197 (7)	−0.4185 (3)	0.80988 (11)	0.0578 (5)
H3	0.1703	−0.5176	0.8487	0.069*
C4	0.09660 (7)	−0.4656 (3)	0.77769 (11)	0.0595 (5)
H4	0.0773	−0.5990	0.7937	0.071*
C5	0.07007 (7)	−0.3131 (3)	0.72164 (11)	0.0567 (5)
H5	0.0328	−0.3425	0.6990	0.068*
C6	0.09996 (7)	−0.1148 (3)	0.69958 (10)	0.0497 (4)
C7	0.07409 (7)	0.0627 (3)	0.64367 (10)	0.0534 (5)
H7	0.0968	0.1816	0.6253	0.057 (5)*
C8	−0.05915 (7)	0.2219 (3)	0.54167 (10)	0.0503 (4)
C9	−0.09482 (7)	0.0371 (3)	0.55988 (10)	0.0566 (5)
H9	−0.0808	−0.0876	0.5926	0.068*
C10	−0.15108 (7)	0.0433 (3)	0.52850 (11)	0.0610 (5)
H10	−0.1758	−0.0798	0.5388	0.073*
C11	−0.17111 (8)	0.2337 (3)	0.48139 (11)	0.0611 (5)
H11	−0.2093	0.2424	0.4600	0.073*
C12	−0.13305 (7)	0.4076 (3)	0.46750 (11)	0.0592 (5)
H12	−0.1466	0.5356	0.4360	0.071*
N1	0.15471 (5)	−0.0724 (2)	0.72889 (8)	0.0509 (4)
N2	0.02035 (6)	0.0560 (2)	0.61977 (8)	0.0552 (4)
N3	−0.00141 (6)	0.2294 (3)	0.57003 (9)	0.0588 (4)
N4	−0.07727 (6)	0.4078 (2)	0.49593 (9)	0.0549 (4)
O1	0.26852 (6)	−0.3248 (2)	0.86646 (8)	0.0732 (4)
H1	0.2962 (11)	−0.408 (4)	0.8416 (16)	0.132 (10)*
H3A	0.0234 (8)	0.344 (3)	0.5493 (12)	0.086 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0537 (11)	0.0719 (11)	0.0624 (13)	0.0080 (9)	−0.0088 (10)	0.0061 (10)
C2	0.0470 (10)	0.0599 (10)	0.0476 (11)	0.0083 (8)	0.0030 (8)	0.0006 (9)
C3	0.0565 (11)	0.0645 (11)	0.0518 (12)	0.0101 (9)	0.0042 (9)	0.0079 (9)
C4	0.0580 (12)	0.0625 (11)	0.0588 (13)	−0.0022 (9)	0.0104 (10)	0.0066 (9)
C5	0.0452 (10)	0.0659 (10)	0.0585 (12)	−0.0014 (8)	0.0033 (9)	0.0049 (10)
C6	0.0452 (10)	0.0567 (10)	0.0463 (11)	0.0032 (8)	0.0017 (8)	0.0009 (8)
C7	0.0479 (11)	0.0598 (10)	0.0513 (12)	−0.0030 (9)	0.0000 (9)	0.0052 (9)
C8	0.0441 (10)	0.0574 (10)	0.0479 (11)	0.0000 (8)	−0.0020 (8)	−0.0026 (9)
C9	0.0520 (11)	0.0597 (10)	0.0567 (12)	−0.0045 (8)	0.0001 (9)	0.0075 (9)
C10	0.0527 (11)	0.0697 (12)	0.0605 (13)	−0.0119 (9)	0.0066 (10)	−0.0004 (10)
C11	0.0420 (10)	0.0782 (12)	0.0611 (13)	−0.0021 (9)	−0.0029 (9)	−0.0008 (10)
C12	0.0489 (11)	0.0639 (11)	0.0627 (13)	0.0042 (9)	−0.0030 (9)	0.0074 (9)
N1	0.0442 (8)	0.0572 (8)	0.0499 (9)	0.0037 (6)	−0.0007 (7)	0.0018 (7)
N2	0.0474 (9)	0.0630 (9)	0.0530 (10)	0.0025 (7)	−0.0031 (7)	0.0066 (7)
N3	0.0456 (9)	0.0620 (9)	0.0657 (11)	−0.0005 (7)	−0.0073 (8)	0.0155 (8)
N4	0.0466 (8)	0.0572 (8)	0.0584 (10)	0.0009 (7)	−0.0053 (7)	0.0069 (7)
O1	0.0615 (9)	0.0894 (9)	0.0648 (10)	0.0171 (7)	−0.0100 (7)	0.0092 (8)

Geometric parameters (Å, º)

C1—O1	1.4043 (19)	C7—H7	0.9300
C1—C2	1.507 (2)	C8—N4	1.3407 (19)
C1—H1A	0.9700	C8—N3	1.386 (2)
C1—H1B	0.9700	C8—C9	1.387 (2)
C2—N1	1.341 (2)	C9—C10	1.367 (2)
C2—C3	1.381 (2)	C9—H9	0.9300
C3—C4	1.377 (2)	C10—C11	1.384 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.376 (2)	C11—C12	1.360 (2)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.388 (2)	C12—N4	1.343 (2)
C5—H5	0.9300	C12—H12	0.9300
C6—N1	1.3454 (19)	N2—N3	1.3508 (18)
C6—C7	1.461 (2)	N3—H3A	0.96 (2)
C7—N2	1.2808 (19)	O1—H1	0.94 (2)
O1—C1—C2	114.21 (15)	C6—C7—H7	119.7
O1—C1—H1A	108.7	N4—C8—N3	114.34 (14)
C2—C1—H1A	108.7	N4—C8—C9	123.33 (15)
O1—C1—H1B	108.7	N3—C8—C9	122.33 (15)
C2—C1—H1B	108.7	C10—C9—C8	118.25 (16)
H1A—C1—H1B	107.6	C10—C9—H9	120.9
N1—C2—C3	122.31 (15)	C8—C9—H9	120.9
N1—C2—C1	114.53 (15)	C9—C10—C11	119.71 (16)
C3—C2—C1	123.15 (15)	C9—C10—H10	120.1
C4—C3—C2	118.97 (16)	C11—C10—H10	120.1
C4—C3—H3	120.5	C12—C11—C10	117.78 (16)
C2—C3—H3	120.5	C12—C11—H11	121.1
C5—C4—C3	119.36 (16)	C10—C11—H11	121.1
C5—C4—H4	120.3	N4—C12—C11	124.74 (16)
C3—C4—H4	120.3	N4—C12—H12	117.6
C4—C5—C6	118.79 (16)	C11—C12—H12	117.6
C4—C5—H5	120.6	C2—N1—C6	118.41 (14)
C6—C5—H5	120.6	C7—N2—N3	117.84 (14)
N1—C6—C5	122.07 (15)	N2—N3—C8	118.81 (15)
N1—C6—C7	115.52 (14)	N2—N3—H3A	120.6 (11)
C5—C6—C7	122.41 (15)	C8—N3—H3A	120.1 (11)
N2—C7—C6	120.58 (16)	C8—N4—C12	116.17 (14)
N2—C7—H7	119.7	C1—O1—H1	109.8 (16)
O1—C1—C2—N1	−174.94 (14)	C9—C10—C11—C12	0.8 (3)
O1—C1—C2—C3	5.3 (3)	C10—C11—C12—N4	0.3 (3)
N1—C2—C3—C4	1.2 (3)	C3—C2—N1—C6	1.0 (2)
C1—C2—C3—C4	−179.02 (17)	C1—C2—N1—C6	−178.81 (16)
C2—C3—C4—C5	−1.5 (3)	C5—C6—N1—C2	−3.0 (2)
C3—C4—C5—C6	−0.4 (3)	C7—C6—N1—C2	176.52 (14)
C4—C5—C6—N1	2.7 (3)	C6—C7—N2—N3	177.93 (14)
C4—C5—C6—C7	−176.73 (16)	C7—N2—N3—C8	178.21 (17)
N1—C6—C7—N2	−171.28 (16)	N4—C8—N3—N2	176.84 (14)
C5—C6—C7—N2	8.2 (3)	C9—C8—N3—N2	−2.8 (3)
N4—C8—C9—C10	1.1 (3)	N3—C8—N4—C12	−179.76 (16)
N3—C8—C9—C10	−179.28 (17)	C9—C8—N4—C12	−0.1 (3)
C8—C9—C10—C11	−1.4 (3)	C11—C12—N4—C8	−0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N4^i	0.96 (2)	2.08 (2)	3.045 (2)	180 (2)
O1—H1···N1^ii	0.94 (2)	1.98 (3)	2.912 (2)	170 (2)

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