N′-(2-Hy­droxy-3-meth­oxy­benzyl­idene)pyrazine-2-carbohydrazide monohydrate

Wang, Z.

doi:10.1107/S2414314619017310

organic compounds

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ISSN: 2414-3146

Volume 5| Part 1| January 2020| x191731

https://doi.org/10.1107/S2414314619017310

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N′-(2-Hydroxy-3-methoxybenzylidene)pyrazine-2-carbohydrazide monohydrate

Zhaodong Wang ^a ^*

^aChongqing Key Laboratory of Environmental, Materials & Remediation Technologies, Chongqing University of Arts and Sciences, Yongchuan, Chongqing, 402160, People's Republic of China
^*Correspondence e-mail: 495481927@qq.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 27 December 2019; accepted 28 December 2019; online 10 January 2020)

In the title hydrated Schiff base, C₁₃H₁₂N₄O₃·H₂O, the dihedral angle between the aromatic rings is 5.06 (11)° and an intramolecular O—H⋯N hydrogen bond closes an S(6) ring. In the crystal, O_w—H⋯O and O_w—H⋯N (w = water) hydrogen bonds link the components into centrosymmetric tetramers (two Schiff bases and two water molecules). Longer N—H⋯O hydrogen bonds link the tetramers into [010] chains. A weak C—H⋯O hydrogen bond and aromatic π–π stacking between the pyrazine and phenyl rings [centroid–centroid separations = 3.604 (2) and 3.715 (2) Å] are also observed.

Keywords: crystal structure; Schiff base; acylhydrazone ligand; hydrogen bonding.

CCDC reference: 1973543

Structure description

Hydrazone-type Schiff base ligands have attracted attention from inorganic chemists because of their simple synthesis and variety arising from changing the aldyhyde or ketone and acylhydrazide precursors. Their applications include molecular switches (Coskun et al., 2012 ), sensors (Albelda et al., 2012 ) and single molecular magnets (SMMs) (Anwar et al., 2018 ). As part of our studies in this area, we now describe the synthesis and structure of the title pyrazine-containing hydrazone, which crystallized as a monohydrate (Fig. 1).

Figure 1
The molecular structure of the title compound showing displacement ellipsoids drawn at the 30% probability level.

The dihedral angle between the aromatic rings is 5.06 (11)° and an intramolecular O2—H2⋯N2 hydrogen bond closes an S(6) ring. The C7—N2 bond length [1.278 (3) Å] is consistent with a normal carbon–nitrogen double bond. In the crystal, O_w—H⋯O and O_w—H⋯N (w = water) hydrogen bonds link the components into centrosymmetric tetramers (two Schiff base and two water molecules). Longer N—H⋯O hydrogen bonds link the tetramers into [010] chains (Table 1, Fig. 2). The packing is consolidated by a weak C—H⋯O hydrogen bond and aromatic π–π stacking between the pyrazine and phenyl rings [centroid–centroid separations = 3.604 (2) and 3.715 (2) Å].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3	0.88	2.34	2.708 (3)	105
N1—H1⋯O4ⁱ	0.88	2.49	3.119 (3)	129
O2—H2⋯N2	0.84	1.94	2.668 (3)	145
O4—H4A⋯O3	0.87	1.99	2.846 (3)	167
O4—H4B⋯N4ⁱⁱ	0.87	2.17	2.998 (3)	160
C13—H13A⋯O2ⁱⁱⁱ	0.98	2.56	3.335 (4)	135
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
The crystal packing viewed along the -axis direction.

Synthesis and crystallization

Pyrazine-2-carbohydrazide (2.76 g, 20 mmol) was reacted with 2-hydroxy-3-methoxybenzaldehyde (3.04 g, 20 mmol) under reflux in 25 ml methanol for 8 h. After cooling and solvent removal by rotary evaporation, a light yellow solid was obtained, which was recrystallized from methanol solution at room temperature to obtain colourless crystals of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₄O₃·H₂O
M_r	290.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	189
a, b, c (Å)	7.018 (3), 9.041 (4), 20.828 (8)
β (°)	91.481 (7)
V (Å³)	1321.1 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.15 × 0.12

Data collection
Diffractometer	Bruker D8 Venture
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.626, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	7707, 2996, 1745
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.161, 1.00
No. of reflections	2996
No. of parameters	195
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1973543

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619017310/hb4335sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619017310/hb4335Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N'-(2-Hydroxy-3-methoxybenzylidene)pyrazine-2-carbohydrazide monohydrate top

Crystal data top

C₁₃H₁₂N₄O₃·H₂O	F(000) = 608
M_r = 290.28	D_x = 1.459 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.018 (3) Å	Cell parameters from 1318 reflections
b = 9.041 (4) Å	θ = 2.5–24.4°
c = 20.828 (8) Å	µ = 0.11 mm⁻¹
β = 91.481 (7)°	T = 189 K
V = 1321.1 (9) Å³	Block, colourless
Z = 4	0.25 × 0.15 × 0.12 mm

Data collection top

Bruker D8 Venture diffractometer	1745 reflections with I > 2σ(I)
Multi–scan	R_int = 0.053
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 27.7°, θ_min = 2.5°
T_min = 0.626, T_max = 0.746	h = −9→8
7707 measured reflections	k = −11→11
2996 independent reflections	l = −18→27

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.161	w = 1/[σ²(F_o²) + (0.076P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2996 reflections	Δρ_max = 0.31 e Å⁻³
195 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.8752 (3)	0.71932 (19)	0.73561 (7)	0.0466 (5)
O2	0.8069 (3)	0.55020 (18)	0.63673 (8)	0.0485 (5)
H2	0.784669	0.504827	0.602149	0.073*
O3	0.6841 (3)	0.2318 (2)	0.50428 (8)	0.0551 (6)
N1	0.7156 (3)	0.4515 (2)	0.45331 (9)	0.0390 (5)
H1	0.713885	0.499088	0.416450	0.047*
N2	0.7502 (3)	0.5261 (2)	0.51003 (9)	0.0380 (5)
N3	0.6642 (3)	0.3166 (2)	0.33806 (9)	0.0366 (5)
N4	0.5903 (3)	0.0122 (2)	0.33186 (10)	0.0411 (5)
C1	0.6523 (3)	0.2336 (3)	0.39063 (10)	0.0324 (6)
C2	0.8247 (3)	0.7542 (3)	0.56268 (10)	0.0329 (6)
C3	0.8709 (3)	0.7883 (3)	0.67721 (11)	0.0325 (6)
C4	0.8336 (3)	0.6947 (3)	0.62434 (11)	0.0336 (6)
C5	0.6843 (3)	0.3044 (3)	0.45503 (11)	0.0370 (6)
C6	0.6124 (3)	0.0832 (3)	0.38743 (11)	0.0378 (6)
H6	0.600418	0.029255	0.426269	0.045*
C7	0.7873 (3)	0.6640 (3)	0.50590 (11)	0.0368 (6)
H7	0.790496	0.708891	0.464695	0.044*
C8	0.8975 (3)	0.9374 (3)	0.66768 (12)	0.0388 (6)
H8	0.924031	1.000252	0.703370	0.047*
C9	0.6062 (4)	0.0945 (3)	0.27911 (12)	0.0400 (6)
H9	0.594317	0.048417	0.238199	0.048*
C10	0.8859 (4)	0.9966 (3)	0.60621 (13)	0.0431 (7)
H10	0.902978	1.099855	0.600130	0.052*
C11	0.8502 (3)	0.9074 (3)	0.55447 (12)	0.0395 (6)
H11	0.842440	0.948922	0.512593	0.047*
C12	0.6397 (3)	0.2452 (3)	0.28243 (11)	0.0387 (6)
H12	0.645434	0.299940	0.243586	0.046*
C13	0.8953 (4)	0.8115 (3)	0.79116 (11)	0.0505 (7)
H13A	1.018576	0.862348	0.790623	0.076*
H13B	0.888839	0.750474	0.829937	0.076*
H13C	0.792400	0.884721	0.790985	0.076*
O4	0.4937 (3)	0.2931 (2)	0.62032 (9)	0.0573 (6)
H4A	0.567749	0.271798	0.588742	0.086*
H4B	0.487099	0.211456	0.642269	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0713 (13)	0.0426 (11)	0.0256 (9)	−0.0046 (9)	−0.0038 (8)	−0.0012 (8)
O2	0.0798 (14)	0.0288 (10)	0.0360 (10)	−0.0038 (9)	−0.0165 (9)	0.0014 (8)
O3	0.0919 (15)	0.0470 (12)	0.0263 (10)	0.0178 (10)	−0.0010 (9)	0.0063 (8)
N1	0.0536 (14)	0.0429 (13)	0.0202 (10)	0.0006 (10)	−0.0043 (9)	−0.0019 (9)
N2	0.0425 (12)	0.0447 (14)	0.0265 (11)	0.0051 (10)	−0.0051 (9)	−0.0052 (9)
N3	0.0413 (12)	0.0401 (12)	0.0283 (11)	0.0018 (9)	−0.0009 (9)	0.0017 (9)
N4	0.0436 (13)	0.0414 (13)	0.0383 (13)	0.0000 (10)	−0.0011 (10)	−0.0032 (10)
C1	0.0333 (13)	0.0379 (14)	0.0259 (12)	0.0062 (10)	−0.0013 (9)	0.0001 (11)
C2	0.0319 (13)	0.0409 (15)	0.0258 (12)	0.0006 (11)	−0.0034 (10)	0.0012 (11)
C3	0.0318 (13)	0.0385 (15)	0.0270 (12)	0.0007 (10)	−0.0024 (10)	0.0033 (10)
C4	0.0363 (14)	0.0288 (14)	0.0353 (14)	0.0023 (10)	−0.0039 (10)	0.0025 (10)
C5	0.0418 (15)	0.0433 (16)	0.0258 (13)	0.0101 (11)	0.0002 (11)	0.0014 (11)
C6	0.0452 (15)	0.0388 (15)	0.0294 (13)	0.0062 (11)	0.0013 (11)	0.0063 (11)
C7	0.0371 (14)	0.0472 (17)	0.0257 (13)	0.0019 (11)	−0.0039 (10)	0.0036 (11)
C8	0.0439 (15)	0.0346 (15)	0.0376 (14)	−0.0042 (11)	−0.0034 (11)	−0.0059 (11)
C9	0.0428 (14)	0.0477 (17)	0.0294 (13)	−0.0024 (12)	−0.0011 (11)	−0.0078 (12)
C10	0.0449 (15)	0.0361 (15)	0.0482 (16)	−0.0040 (12)	−0.0038 (12)	0.0050 (12)
C11	0.0418 (14)	0.0422 (16)	0.0341 (14)	−0.0046 (12)	−0.0044 (11)	0.0115 (11)
C12	0.0462 (15)	0.0438 (16)	0.0258 (13)	−0.0019 (12)	−0.0037 (11)	0.0014 (11)
C13	0.0620 (19)	0.0581 (19)	0.0314 (14)	0.0005 (14)	−0.0002 (13)	−0.0079 (13)
O4	0.0784 (15)	0.0496 (12)	0.0441 (12)	0.0017 (10)	0.0057 (10)	0.0024 (9)

Geometric parameters (Å, º) top

O1—C3	1.367 (3)	C3—C4	1.408 (3)
O1—C13	1.430 (3)	C3—C8	1.376 (3)
O2—H2	0.8400	C6—H6	0.9500
O2—C4	1.346 (3)	C7—H7	0.9500
O3—C5	1.218 (3)	C8—H8	0.9500
N1—H1	0.8800	C8—C10	1.388 (4)
N1—N2	1.376 (3)	C9—H9	0.9500
N1—C5	1.348 (3)	C9—C12	1.385 (4)
N2—C7	1.278 (3)	C10—H10	0.9500
N3—C1	1.332 (3)	C10—C11	1.364 (4)
N3—C12	1.333 (3)	C11—H11	0.9500
N4—C6	1.329 (3)	C12—H12	0.9500
N4—C9	1.334 (3)	C13—H13A	0.9800
C1—C5	1.498 (3)	C13—H13B	0.9800
C1—C6	1.390 (3)	C13—H13C	0.9800
C2—C4	1.393 (3)	O4—H4A	0.8702
C2—C7	1.455 (3)	O4—H4B	0.8697
C2—C11	1.407 (3)

C3—O1—C13	117.0 (2)	N2—C7—C2	121.7 (2)
C4—O2—H2	109.5	N2—C7—H7	119.1
N2—N1—H1	120.5	C2—C7—H7	119.1
C5—N1—H1	120.5	C3—C8—H8	119.8
C5—N1—N2	119.1 (2)	C3—C8—C10	120.4 (2)
C7—N2—N1	116.9 (2)	C10—C8—H8	119.8
C1—N3—C12	115.6 (2)	N4—C9—H9	119.2
C6—N4—C9	116.0 (2)	N4—C9—C12	121.7 (2)
N3—C1—C5	119.0 (2)	C12—C9—H9	119.2
N3—C1—C6	121.9 (2)	C8—C10—H10	119.8
C6—C1—C5	119.1 (2)	C11—C10—C8	120.4 (2)
C4—C2—C7	122.4 (2)	C11—C10—H10	119.8
C4—C2—C11	119.3 (2)	C2—C11—H11	119.8
C11—C2—C7	118.3 (2)	C10—C11—C2	120.5 (2)
O1—C3—C4	114.9 (2)	C10—C11—H11	119.8
O1—C3—C8	125.2 (2)	N3—C12—C9	122.5 (2)
C8—C3—C4	120.0 (2)	N3—C12—H12	118.7
O2—C4—C2	123.3 (2)	C9—C12—H12	118.7
O2—C4—C3	117.2 (2)	O1—C13—H13A	109.5
C2—C4—C3	119.4 (2)	O1—C13—H13B	109.5
O3—C5—N1	123.9 (2)	O1—C13—H13C	109.5
O3—C5—C1	121.4 (2)	H13A—C13—H13B	109.5
N1—C5—C1	114.7 (2)	H13A—C13—H13C	109.5
N4—C6—C1	122.2 (2)	H13B—C13—H13C	109.5
N4—C6—H6	118.9	H4A—O4—H4B	104.5
C1—C6—H6	118.9

O1—C3—C4—O2	−0.1 (3)	C6—N4—C9—C12	−1.3 (4)
O1—C3—C4—C2	179.5 (2)	C6—C1—C5—O3	3.2 (4)
O1—C3—C8—C10	−178.5 (2)	C6—C1—C5—N1	−177.8 (2)
N1—N2—C7—C2	179.5 (2)	C7—C2—C4—O2	−0.6 (4)
N2—N1—C5—O3	0.2 (4)	C7—C2—C4—C3	179.8 (2)
N2—N1—C5—C1	−178.74 (19)	C7—C2—C11—C10	−179.9 (2)
N3—C1—C5—O3	−176.4 (2)	C8—C3—C4—O2	−179.3 (2)
N3—C1—C5—N1	2.6 (3)	C8—C3—C4—C2	0.2 (3)
N3—C1—C6—N4	2.4 (4)	C8—C10—C11—C2	0.0 (4)
N4—C9—C12—N3	2.2 (4)	C9—N4—C6—C1	−0.9 (4)
C1—N3—C12—C9	−0.7 (3)	C11—C2—C4—O2	178.5 (2)
C3—C8—C10—C11	−0.8 (4)	C11—C2—C4—C3	−1.0 (3)
C4—C2—C7—N2	3.9 (4)	C11—C2—C7—N2	−175.3 (2)
C4—C2—C11—C10	0.9 (4)	C12—N3—C1—C5	178.1 (2)
C4—C3—C8—C10	0.7 (4)	C12—N3—C1—C6	−1.5 (3)
C5—N1—N2—C7	177.0 (2)	C13—O1—C3—C4	−174.5 (2)
C5—C1—C6—N4	−177.1 (2)	C13—O1—C3—C8	4.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.88	2.34	2.708 (3)	105
N1—H1···O4ⁱ	0.88	2.49	3.119 (3)	129
O2—H2···N2	0.84	1.94	2.668 (3)	145
O4—H4A···O3	0.87	1.99	2.846 (3)	167
O4—H4B···N4ⁱⁱ	0.87	2.17	2.998 (3)	160
C13—H13A···O2ⁱⁱⁱ	0.98	2.56	3.335 (4)	135

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

Funding information

The author would like to thank the major cultivation project of Chongqing University of Arts and Sciences (No. P2017CH10) for financial support.

References

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