(E)-N′-(1,3-Benzodioxol-5-ylmethyl­ene)nicotinohydrazide monohydrate

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

doi:10.1107/S1600536809034503

organic compounds

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doi:10.1107/S1600536809034503

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(E)-N′-(1,3-Benzodioxol-5-ylmethylene)nicotinohydrazide monohydrate

Feng-Yu Bao,^a ^* Hai-Yan Zhang,^a Ying-Xia Zhou ^a and Su Hui ^a

^aDepartment of Applied Chemistry, College of Sciences, Henan Agricultural University, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: bfyu2008@126.com

(Received 21 August 2009; accepted 28 August 2009; online 5 September 2009)

In the title compound, C₁₄H₁₁N₃O₃·H₂O, the planar [maximum deviation 0.135 (1) Å] 1,3-benzodioxole ring system is oriented at a dihedral angle of 13.93 (7)° with respect to the pyridine ring. Extensive intermolecular N—H⋯O, O—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

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

Experimental

Crystal data

C₁₄H₁₁N₃O₃·H₂O
M_r = 287.28
Monoclinic, P 2₁ /n
a = 8.6414 (2) Å
b = 12.0874 (2) Å
c = 13.4464 (3) Å
β = 103.161 (1)°
V = 1367.61 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.26 × 0.21 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.974, T_max = 0.982
19494 measured reflections
2691 independent reflections
1839 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.04
2691 reflections
199 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4ⁱ	0.86	2.04	2.8819 (17)	164
O4—H4A⋯N3	0.848 (9)	1.980 (17)	2.825 (2)	174 (2)
O4—H4B⋯O3ⁱⁱ	0.839 (9)	2.106 (15)	2.9019 (19)	158.2 (16)
C3—H3B⋯O3ⁱⁱⁱ	0.97	2.57	3.495 (2)	160
C8—H8A⋯O4ⁱ	0.93	2.51	3.312 (2)	144
C11—H11A⋯O4ⁱ	0.93	2.45	3.324 (2)	156
Symmetry codes: (i) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) -x+1, -y+1, -z.

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/S1600536809034503/xu2599sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034503/xu2599Isup2.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 synthesized the title compound and report here its crystal structure.

The title molecule crystallizes in the E conformation (Fig. 1), with the N2—N1—C8—C7 torsion angle of 179.60 (13)°. The dihedral angle between the 1,3-benzodioxole ring system and the pyridine ring is 13.93 (7)°. The extensive intermolecular classic N—H···O, O—H···O, O—H···N and weak C—H···O hydrogen bonding is present in the crystal structure (Table 1 and Fig. 2).

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 solution was stirred at 351 K for several min, and then the 1,3-benzodioxole-5-carbaldehyde (1 mmol, 0.150 g) in ethanol (8 mm l) was added dropwise. The mixture was refluxed for 2 h. The solid product was isolated and recrystallized from methanol-water solution. Colourless single crystals of the title compound 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.
	Fig. 2. The unit cell packing diagram showing intermolecular hydrogen bonding as dashed lines.

(E)-N'-(1,3-Benzodioxol-5-ylmethylene)nicotinohydrazide monohydrate top

Crystal data top

C₁₄H₁₁N₃O₃·H₂O	F(000) = 600
M_r = 287.28	D_x = 1.395 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2884 reflections
a = 8.6414 (2) Å	θ = 2.3–26.0°
b = 12.0874 (2) Å	µ = 0.11 mm⁻¹
c = 13.4464 (3) Å	T = 293 K
β = 103.161 (1)°	Block, colourless
V = 1367.61 (5) Å³	0.26 × 0.21 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2691 independent reflections
Radiation source: fine-focus sealed tube	1839 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
T_min = 0.974, T_max = 0.982	k = −14→14
19494 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0582P)² + 0.0682P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.010
2691 reflections	Δρ_max = 0.15 e Å⁻³
199 parameters	Δρ_min = −0.13 e Å⁻³
3 restraints	Extinction correction: SHELXTL (Version 5.1; Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (14)

Crystal data top

C₁₄H₁₁N₃O₃·H₂O	V = 1367.61 (5) Å³
M_r = 287.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6414 (2) Å	µ = 0.11 mm⁻¹
b = 12.0874 (2) Å	T = 293 K
c = 13.4464 (3) Å	0.26 × 0.21 × 0.17 mm
β = 103.161 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2691 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1839 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.982	R_int = 0.044
19494 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.15 e Å⁻³
2691 reflections	Δρ_min = −0.13 e Å⁻³
199 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
N1	0.25573 (14)	0.30595 (11)	0.16863 (10)	0.0528 (4)
C7	0.46242 (17)	0.23623 (12)	0.09399 (11)	0.0469 (4)
O3	0.08396 (13)	0.45982 (9)	0.23857 (10)	0.0702 (4)
C10	−0.09502 (16)	0.32960 (12)	0.28168 (11)	0.0442 (4)
O2	0.84690 (15)	0.27321 (11)	−0.03215 (11)	0.0807 (4)
N2	0.12618 (14)	0.27993 (10)	0.20830 (10)	0.0516 (4)
H2A	0.0972	0.2122	0.2116	0.062*
C2	0.65230 (18)	0.34247 (13)	0.03595 (12)	0.0522 (4)
N3	−0.33050 (15)	0.39773 (11)	0.32710 (11)	0.0596 (4)
O1	0.73361 (16)	0.43293 (10)	0.01301 (11)	0.0842 (5)
C6	0.53331 (19)	0.14169 (13)	0.06740 (13)	0.0544 (4)
H6A	0.4908	0.0732	0.0781	0.065*
C8	0.32492 (19)	0.22390 (13)	0.13835 (12)	0.0530 (4)
H8A	0.2860	0.1532	0.1449	0.064*
C11	−0.12747 (19)	0.22473 (13)	0.31162 (13)	0.0523 (4)
H11A	−0.0606	0.1659	0.3059	0.063*
C5	0.66608 (19)	0.14538 (13)	0.02518 (13)	0.0576 (5)
H5A	0.7142	0.0814	0.0084	0.069*
C13	−0.35719 (19)	0.29587 (15)	0.35623 (13)	0.0607 (5)
H13A	−0.4466	0.2835	0.3822	0.073*
C4	0.72117 (19)	0.24715 (14)	0.00991 (13)	0.0530 (4)
C9	0.04620 (17)	0.36199 (12)	0.24153 (12)	0.0489 (4)
C1	0.52308 (19)	0.34048 (12)	0.07778 (12)	0.0520 (4)
H1B	0.4771	0.4053	0.0948	0.062*
C12	−0.26006 (19)	0.20836 (14)	0.34996 (13)	0.0606 (5)
H12A	−0.2834	0.1384	0.3714	0.073*
C14	−0.20100 (18)	0.41282 (13)	0.29066 (12)	0.0523 (4)
H14A	−0.1805	0.4837	0.2700	0.063*
C3	0.8597 (2)	0.38998 (17)	−0.02752 (16)	0.0772 (6)
H3B	0.8535	0.4197	−0.0953	0.093*
H3C	0.9612	0.4112	0.0157	0.093*
O4	−0.59280 (17)	0.54330 (10)	0.28071 (14)	0.0854 (5)
H4A	−0.5119 (16)	0.5021 (15)	0.2985 (18)	0.112 (8)*
H4B	−0.6745 (16)	0.5040 (15)	0.2633 (16)	0.102 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0450 (7)	0.0537 (8)	0.0663 (9)	−0.0044 (6)	0.0260 (7)	−0.0009 (7)
C7	0.0436 (8)	0.0483 (9)	0.0525 (9)	−0.0015 (7)	0.0187 (7)	−0.0012 (7)
O3	0.0679 (8)	0.0461 (7)	0.1111 (10)	−0.0071 (5)	0.0505 (7)	−0.0048 (6)
C10	0.0375 (8)	0.0476 (9)	0.0491 (9)	−0.0033 (6)	0.0135 (7)	−0.0031 (7)
O2	0.0748 (9)	0.0758 (9)	0.1108 (11)	−0.0141 (7)	0.0614 (8)	−0.0153 (7)
N2	0.0440 (7)	0.0454 (7)	0.0729 (9)	−0.0049 (6)	0.0294 (7)	−0.0021 (6)
C2	0.0550 (10)	0.0463 (9)	0.0600 (10)	−0.0091 (7)	0.0234 (8)	−0.0017 (7)
N3	0.0461 (8)	0.0603 (9)	0.0782 (10)	0.0029 (7)	0.0260 (7)	−0.0028 (7)
O1	0.0930 (10)	0.0566 (8)	0.1237 (11)	−0.0162 (7)	0.0675 (9)	−0.0050 (7)
C6	0.0545 (10)	0.0448 (9)	0.0698 (11)	−0.0030 (7)	0.0262 (8)	−0.0015 (8)
C8	0.0500 (9)	0.0483 (9)	0.0663 (11)	−0.0057 (7)	0.0249 (8)	−0.0030 (8)
C11	0.0499 (9)	0.0474 (9)	0.0645 (10)	0.0006 (7)	0.0235 (8)	0.0002 (8)
C5	0.0563 (10)	0.0476 (10)	0.0754 (12)	0.0023 (7)	0.0286 (9)	−0.0088 (8)
C13	0.0483 (10)	0.0688 (11)	0.0733 (12)	−0.0067 (8)	0.0312 (9)	−0.0040 (9)
C4	0.0455 (9)	0.0601 (10)	0.0597 (10)	−0.0035 (7)	0.0252 (8)	−0.0067 (8)
C9	0.0448 (9)	0.0466 (9)	0.0593 (10)	−0.0027 (7)	0.0200 (8)	0.0003 (7)
C1	0.0540 (9)	0.0454 (9)	0.0621 (10)	0.0009 (7)	0.0245 (8)	−0.0062 (7)
C12	0.0624 (11)	0.0522 (10)	0.0754 (12)	−0.0086 (8)	0.0329 (10)	0.0020 (8)
C14	0.0472 (9)	0.0467 (9)	0.0672 (10)	0.0015 (7)	0.0216 (8)	0.0019 (8)
C3	0.0742 (13)	0.0751 (13)	0.0953 (15)	−0.0113 (11)	0.0461 (11)	0.0042 (11)
O4	0.0518 (8)	0.0474 (7)	0.1622 (15)	0.0012 (6)	0.0353 (9)	0.0012 (8)

Geometric parameters (Å, º) top

N1—C8	1.2719 (19)	O1—C3	1.423 (2)
N1—N2	1.3815 (16)	C6—C5	1.392 (2)
C7—C6	1.382 (2)	C6—H6A	0.9300
C7—C1	1.401 (2)	C8—H8A	0.9300
C7—C8	1.453 (2)	C11—C12	1.374 (2)
O3—C9	1.2299 (17)	C11—H11A	0.9300
C10—C11	1.378 (2)	C5—C4	1.351 (2)
C10—C14	1.384 (2)	C5—H5A	0.9300
C10—C9	1.4946 (19)	C13—C12	1.365 (2)
O2—C4	1.3709 (18)	C13—H13A	0.9300
O2—C3	1.416 (2)	C1—H1B	0.9300
N2—C9	1.3423 (18)	C12—H12A	0.9300
N2—H2A	0.8600	C14—H14A	0.9300
C2—C1	1.360 (2)	C3—H3B	0.9700
C2—O1	1.3723 (18)	C3—H3C	0.9700
C2—C4	1.378 (2)	O4—H4A	0.848 (9)
N3—C13	1.328 (2)	O4—H4B	0.839 (9)
N3—C14	1.3324 (19)

C8—N1—N2	115.31 (13)	C6—C5—H5A	121.9
C6—C7—C1	120.01 (14)	N3—C13—C12	123.35 (15)
C6—C7—C8	118.26 (13)	N3—C13—H13A	118.3
C1—C7—C8	121.73 (14)	C12—C13—H13A	118.3
C11—C10—C14	117.41 (13)	C5—C4—O2	127.70 (15)
C11—C10—C9	125.71 (14)	C5—C4—C2	122.33 (14)
C14—C10—C9	116.88 (13)	O2—C4—C2	109.96 (14)
C4—O2—C3	105.81 (12)	O3—C9—N2	122.63 (13)
C9—N2—N1	118.97 (12)	O3—C9—C10	120.53 (13)
C9—N2—H2A	120.5	N2—C9—C10	116.83 (13)
N1—N2—H2A	120.5	C2—C1—C7	116.86 (14)
C1—C2—O1	128.15 (14)	C2—C1—H1B	121.6
C1—C2—C4	122.21 (14)	C7—C1—H1B	121.6
O1—C2—C4	109.64 (13)	C13—C12—C11	119.27 (16)
C13—N3—C14	116.88 (14)	C13—C12—H12A	120.4
C2—O1—C3	105.75 (13)	C11—C12—H12A	120.4
C7—C6—C5	122.29 (14)	N3—C14—C10	124.09 (15)
C7—C6—H6A	118.9	N3—C14—H14A	118.0
C5—C6—H6A	118.9	C10—C14—H14A	118.0
N1—C8—C7	122.63 (15)	O2—C3—O1	108.74 (13)
N1—C8—H8A	118.7	O2—C3—H3B	109.9
C7—C8—H8A	118.7	O1—C3—H3B	109.9
C12—C11—C10	118.99 (15)	O2—C3—H3C	109.9
C12—C11—H11A	120.5	O1—C3—H3C	109.9
C10—C11—H11A	120.5	H3B—C3—H3C	108.3
C4—C5—C6	116.29 (14)	H4A—O4—H4B	109.5 (18)
C4—C5—H5A	121.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.86	2.04	2.8819 (17)	164
O4—H4A···N3	0.85 (1)	1.98 (2)	2.825 (2)	174 (2)
O4—H4B···O3ⁱⁱ	0.84 (1)	2.11 (2)	2.9019 (19)	158 (2)
C3—H3B···O3ⁱⁱⁱ	0.97	2.57	3.495 (2)	160
C8—H8A···O4ⁱ	0.93	2.51	3.312 (2)	144
C11—H11A···O4ⁱ	0.93	2.45	3.324 (2)	156

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₃·H₂O
M_r	287.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.6414 (2), 12.0874 (2), 13.4464 (3)
β (°)	103.161 (1)
V (Å³)	1367.61 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.26 × 0.21 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.974, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	19494, 2691, 1839
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.04
No. of reflections	2691
No. of parameters	199
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13

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
N2—H2A···O4ⁱ	0.86	2.04	2.8819 (17)	164
O4—H4A···N3	0.848 (9)	1.980 (17)	2.825 (2)	174 (2)
O4—H4B···O3ⁱⁱ	0.839 (9)	2.106 (15)	2.9019 (19)	158.2 (16)
C3—H3B···O3ⁱⁱⁱ	0.97	2.57	3.495 (2)	160
C8—H8A···O4ⁱ	0.93	2.51	3.312 (2)	144
C11—H11A···O4ⁱ	0.93	2.45	3.324 (2)	156

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

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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doi:10.1107/S1600536809034503

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