N′-(3-Bromo-4-methoxy­benzyl­idene)nicotinohydrazide monohydrate

Bao, F.-Y.; Ding, X.-S.; Zhang, H.-Y.; Zhou, Y.-X.

doi:10.1107/S160053680903400X

organic compounds

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doi:10.1107/S160053680903400X

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N′-(3-Bromo-4-methoxybenzylidene)nicotinohydrazide monohydrate

Feng-Yu Bao,^a ^* Xing-Shun Ding,^b Hai-Yan Zhang ^a and Ying-Xia Zhou ^a

^aDepartment of Applied Chemistry, College of Sciences, Henan Agricultural University, Zhengzhou 450002, People's Republic of China, and ^bLiangbaosi First School, Jiaxiang County, Shandong Province 272404, People's Republic of China
^*Correspondence e-mail: bfyu2008@126.com

(Received 21 August 2009; accepted 25 August 2009; online 29 August 2009)

In the title compound, C₁₄H₁₂BrN₃O₂·H₂O, the benzene ring is oriented at a dihedral angle of 39.66 (11)° with respect to the pyridine ring. The solvent water molecule links with the organic compound via O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonding.

Related literature

For applications of Schiff base compounds, see: Kahwa et al. (1986 ); Santos et al. (2001 ).

Experimental

Crystal data

C₁₄H₁₂BrN₃O₂·H₂O
M_r = 352.18
Monoclinic, P 2₁ /c
a = 7.7979 (1) Å
b = 12.5678 (2) Å
c = 14.9419 (3) Å
β = 97.449 (1)°
V = 1451.98 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.85 mm⁻¹
T = 296 K
0.43 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.400, T_max = 0.535
12611 measured reflections
3149 independent reflections
2525 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.069
S = 1.01
3149 reflections
198 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N3	0.85 (2)	2.05 (2)	2.886 (2)	168 (2)
O2—H2B⋯O1ⁱ	0.82 (3)	2.47 (3)	3.118 (2)	136 (2)
O2—H2B⋯N1ⁱ	0.82 (3)	2.43 (3)	3.197 (2)	156 (3)
N2—H2⋯O2ⁱⁱ	0.86	2.18	2.982 (2)	155
Symmetry codes: (i) -x, -y+1, -z-1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903400X/xu2597sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903400X/xu2597Isup2.hkl

checkCIF report

Comment top

The chemistry of Schiff bases has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our interest in the coordination chemistry of Schiff bases, we have recently synthesized the title compound and report here its crystal structure.

The title molecule crystallizes in the E conformation, with the C8—N1—N2—C9 torsion angle of 170.02 (19)°. The molecular is non-planar, there is a dihedral angle of 39.66 (11)° between the benzene ring and the pyridine ring. In the crystal structure, the lattice water molecule links with the organic compound via O—H···O, O—H···N and N—H···O hydrogen bonding.

Related literature top

For applications of Schiff base compounds, see: Kahwa et al. (1986); Santos et al. (2001).

Experimental top

Nicotinohydrazide (1 mmol, 0.137 g) was dissolved in ethanol (15 ml). The mixture was stirred for several min at 351 K, then 3-bromo-4-methoxybenzaldehyde (1 mmol, 0.215 g) in ethanol (8 mm l) was added dropwise and the mixture was refluxed for 2 h. The solid product was isolated and recrystallized from methanol, colourless single crystals were obtained after 3 d.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

N'-(3-Bromo-4-methoxybenzylidene)nicotinohydrazide monohydrate top

Crystal data top

C₁₄H₁₂BrN₃O₂·H₂O	F(000) = 712
M_r = 352.18	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4706 reflections
a = 7.7979 (1) Å	θ = 3.1–27.0°
b = 12.5678 (2) Å	µ = 2.85 mm⁻¹
c = 14.9419 (3) Å	T = 296 K
β = 97.449 (1)°	Block, colourless
V = 1451.98 (4) Å³	0.43 × 0.28 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3149 independent reflections
Radiation source: fine-focus sealed tube	2525 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→9
T_min = 0.400, T_max = 0.535	k = −16→16
12611 measured reflections	l = −19→16

Refinement top

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0354P)² + 0.4288P] where P = (F_o² + 2F_c²)/3
3149 reflections	(Δ/σ)_max < 0.001
198 parameters	Δρ_max = 0.41 e Å⁻³
2 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₁₂BrN₃O₂·H₂O	V = 1451.98 (4) Å³
M_r = 352.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7979 (1) Å	µ = 2.85 mm⁻¹
b = 12.5678 (2) Å	T = 296 K
c = 14.9419 (3) Å	0.43 × 0.28 × 0.22 mm
β = 97.449 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3149 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2525 reflections with I > 2σ(I)
T_min = 0.400, T_max = 0.535	R_int = 0.027
12611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	2 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.41 e Å⁻³
3149 reflections	Δρ_min = −0.30 e Å⁻³
198 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.38290 (3)	0.882695 (16)	0.139661 (15)	0.04825 (10)
O1	−0.0836 (2)	0.53946 (11)	−0.37189 (9)	0.0481 (4)
N1	0.0118 (2)	0.66340 (13)	−0.22564 (10)	0.0364 (4)
C2	0.2856 (2)	0.77093 (14)	0.06618 (12)	0.0319 (4)
C6	0.1504 (3)	0.70831 (15)	−0.07779 (12)	0.0330 (4)
N2	−0.0635 (2)	0.70309 (13)	−0.30777 (10)	0.0373 (4)
H2	−0.0792	0.7704	−0.3150	0.045*
C5	0.1501 (3)	0.60611 (15)	−0.04249 (14)	0.0389 (5)
H5A	0.1064	0.5501	−0.0792	0.047*
O	0.3473 (2)	0.65767 (12)	0.19064 (9)	0.0467 (4)
N3	−0.2839 (3)	0.66239 (14)	−0.61976 (11)	0.0445 (4)
C13	−0.3787 (3)	0.81441 (17)	−0.54493 (14)	0.0416 (5)
H13A	−0.4406	0.8779	−0.5484	0.050*
C1	0.2194 (3)	0.79090 (15)	−0.02219 (12)	0.0344 (4)
H1A	0.2207	0.8598	−0.0448	0.041*
C14	−0.2933 (3)	0.78026 (16)	−0.46379 (13)	0.0373 (4)
H14A	−0.2956	0.8207	−0.4118	0.045*
C12	−0.3718 (3)	0.75404 (18)	−0.62074 (13)	0.0438 (5)
H12A	−0.4306	0.7777	−0.6752	0.053*
C11	−0.2044 (3)	0.62932 (16)	−0.54085 (13)	0.0386 (5)
H11A	−0.1453	0.5649	−0.5392	0.046*
C10	−0.2041 (2)	0.68508 (15)	−0.46049 (12)	0.0313 (4)
C3	0.2824 (3)	0.66925 (15)	0.10238 (12)	0.0336 (4)
C4	0.2141 (3)	0.58670 (16)	0.04669 (13)	0.0386 (5)
H4A	0.2116	0.5180	0.0696	0.046*
C8	0.0758 (3)	0.73423 (16)	−0.17017 (13)	0.0373 (4)
H8A	0.0751	0.8048	−0.1890	0.045*
C7	0.3529 (4)	0.55397 (18)	0.22835 (15)	0.0573 (7)
H7A	0.4014	0.5573	0.2907	0.086*
H7B	0.4233	0.5089	0.1962	0.086*
H7C	0.2379	0.5255	0.2237	0.086*
C9	−0.1121 (3)	0.63517 (15)	−0.37660 (12)	0.0332 (4)
O2	−0.1669 (3)	0.57231 (13)	−0.77890 (10)	0.0521 (4)
H2A	−0.214 (3)	0.5932 (19)	−0.7336 (13)	0.068 (9)*
H2B	−0.110 (3)	0.519 (2)	−0.7634 (19)	0.072 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.06384 (18)	0.03325 (12)	0.04243 (13)	−0.00024 (10)	−0.01295 (10)	−0.01048 (9)
O1	0.0686 (11)	0.0340 (8)	0.0379 (8)	0.0075 (7)	−0.0074 (7)	−0.0026 (6)
N1	0.0453 (10)	0.0359 (8)	0.0259 (8)	0.0031 (8)	−0.0035 (7)	0.0004 (7)
C2	0.0353 (11)	0.0284 (9)	0.0298 (9)	−0.0003 (8)	−0.0036 (8)	−0.0066 (7)
C6	0.0352 (11)	0.0358 (10)	0.0265 (9)	0.0022 (8)	−0.0014 (8)	−0.0018 (8)
N2	0.0513 (11)	0.0315 (8)	0.0260 (8)	0.0006 (7)	−0.0065 (7)	0.0007 (6)
C5	0.0460 (13)	0.0336 (10)	0.0345 (10)	−0.0031 (9)	−0.0050 (9)	−0.0054 (8)
O	0.0678 (11)	0.0386 (8)	0.0292 (7)	0.0033 (7)	−0.0105 (7)	0.0033 (6)
N3	0.0600 (12)	0.0418 (10)	0.0293 (8)	−0.0012 (9)	−0.0031 (8)	−0.0037 (7)
C13	0.0437 (13)	0.0374 (10)	0.0419 (11)	0.0047 (9)	−0.0008 (9)	0.0031 (9)
C1	0.0391 (12)	0.0299 (9)	0.0323 (9)	0.0027 (8)	−0.0020 (8)	0.0009 (8)
C14	0.0414 (12)	0.0377 (10)	0.0322 (10)	−0.0007 (9)	0.0021 (8)	−0.0052 (8)
C12	0.0507 (14)	0.0457 (12)	0.0318 (10)	−0.0048 (10)	−0.0074 (9)	0.0049 (9)
C11	0.0499 (13)	0.0342 (10)	0.0300 (10)	−0.0010 (9)	−0.0011 (9)	−0.0027 (8)
C10	0.0328 (11)	0.0329 (9)	0.0270 (9)	−0.0053 (8)	−0.0003 (8)	−0.0013 (7)
C3	0.0371 (11)	0.0350 (10)	0.0270 (9)	0.0045 (9)	−0.0022 (8)	0.0004 (8)
C4	0.0500 (13)	0.0282 (9)	0.0353 (10)	−0.0017 (9)	−0.0028 (9)	0.0032 (8)
C8	0.0429 (12)	0.0372 (10)	0.0299 (9)	0.0001 (9)	−0.0020 (8)	0.0005 (8)
C7	0.0838 (19)	0.0451 (13)	0.0387 (12)	0.0038 (12)	−0.0086 (11)	0.0144 (10)
C9	0.0384 (11)	0.0335 (10)	0.0270 (9)	−0.0006 (8)	0.0016 (8)	−0.0018 (7)
O2	0.0845 (13)	0.0375 (8)	0.0337 (8)	0.0076 (9)	0.0059 (8)	0.0042 (7)

Geometric parameters (Å, º) top

Br1—C2	1.8810 (17)	C13—C14	1.374 (3)
O1—C9	1.224 (2)	C13—H13A	0.9300
N1—C8	1.273 (2)	C1—H1A	0.9300
N1—N2	1.383 (2)	C14—C10	1.382 (3)
C2—C1	1.377 (2)	C14—H14A	0.9300
C2—C3	1.389 (3)	C12—H12A	0.9300
C6—C5	1.389 (3)	C11—C10	1.390 (3)
C6—C1	1.393 (3)	C11—H11A	0.9300
C6—C8	1.463 (3)	C10—C9	1.499 (3)
N2—C9	1.352 (2)	C3—C4	1.392 (3)
N2—H2	0.8600	C4—H4A	0.9300
C5—C4	1.383 (3)	C8—H8A	0.9300
C5—H5A	0.9300	C7—H7A	0.9600
O—C3	1.358 (2)	C7—H7B	0.9600
O—C7	1.418 (3)	C7—H7C	0.9600
N3—C11	1.326 (3)	O2—H2A	0.85 (2)
N3—C12	1.340 (3)	O2—H2B	0.82 (3)
C13—C12	1.370 (3)

C8—N1—N2	114.26 (16)	C13—C12—H12A	118.6
C1—C2—C3	121.17 (17)	N3—C11—C10	123.96 (19)
C1—C2—Br1	119.76 (14)	N3—C11—H11A	118.0
C3—C2—Br1	119.07 (13)	C10—C11—H11A	118.0
C5—C6—C1	118.83 (17)	C14—C10—C11	117.46 (18)
C5—C6—C8	122.96 (17)	C14—C10—C9	125.20 (17)
C1—C6—C8	118.18 (17)	C11—C10—C9	117.30 (17)
C9—N2—N1	119.48 (16)	O—C3—C2	116.98 (17)
C9—N2—H2	120.3	O—C3—C4	124.49 (17)
N1—N2—H2	120.3	C2—C3—C4	118.54 (17)
C4—C5—C6	120.74 (18)	C5—C4—C3	120.46 (18)
C4—C5—H5A	119.6	C5—C4—H4A	119.8
C6—C5—H5A	119.6	C3—C4—H4A	119.8
C3—O—C7	118.23 (16)	N1—C8—C6	122.20 (18)
C11—N3—C12	117.32 (17)	N1—C8—H8A	118.9
C12—C13—C14	119.3 (2)	C6—C8—H8A	118.9
C12—C13—H13A	120.3	O—C7—H7A	109.5
C14—C13—H13A	120.3	O—C7—H7B	109.5
C2—C1—C6	120.25 (17)	H7A—C7—H7B	109.5
C2—C1—H1A	119.9	O—C7—H7C	109.5
C6—C1—H1A	119.9	H7A—C7—H7C	109.5
C13—C14—C10	119.09 (19)	H7B—C7—H7C	109.5
C13—C14—H14A	120.5	O1—C9—N2	123.08 (18)
C10—C14—H14A	120.5	O1—C9—C10	121.55 (17)
N3—C12—C13	122.83 (19)	N2—C9—C10	115.38 (16)
N3—C12—H12A	118.6	H2A—O2—H2B	107 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N3	0.85 (2)	2.05 (2)	2.886 (2)	168 (2)
O2—H2B···O1ⁱ	0.82 (3)	2.47 (3)	3.118 (2)	136 (2)
O2—H2B···N1ⁱ	0.82 (3)	2.43 (3)	3.197 (2)	156 (3)
N2—H2···O2ⁱⁱ	0.86	2.18	2.982 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂BrN₃O₂·H₂O
M_r	352.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.7979 (1), 12.5678 (2), 14.9419 (3)
β (°)	97.449 (1)
V (Å³)	1451.98 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.85
Crystal size (mm)	0.43 × 0.28 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.400, 0.535
No. of measured, independent and observed [I > 2σ(I)] reflections	12611, 3149, 2525
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.069, 1.01
No. of reflections	3149
No. of parameters	198
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N3	0.85 (2)	2.05 (2)	2.886 (2)	168 (2)
O2—H2B···O1ⁱ	0.82 (3)	2.47 (3)	3.118 (2)	136 (2)
O2—H2B···N1ⁱ	0.82 (3)	2.43 (3)	3.197 (2)	156 (3)
N2—H2···O2ⁱⁱ	0.86	2.18	2.982 (2)	155

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

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185. CrossRef CAS Web of Science Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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