4-{[(5-Methyl-2-fur­yl)methyl­ene]hydrazinocarbon­yl}pyridinium chloride monohydrate

Li, L.-M.; Jian, F.-F.; Liu, L.

doi:10.1107/S1600536809028426

organic compounds

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Volume 65| Part 8| August 2009| Page o1983

doi:10.1107/S1600536809028426

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4-{[(5-Methyl-2-furyl)methylene]hydrazinocarbonyl}pyridinium chloride monohydrate

Li-Min Li,^a Fang-Fang Jian ^b ^* and Li Liu ^a

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 15 July 2009; accepted 18 July 2009; online 25 July 2009)

The title compound, C₁₂H₁₂N₃O₂⁺·Cl⁻·H₂O, was prepared by the reaction of N′-[(5-methyl-2-furyl)methylene]isonicotinohydrazide and hydrochloric acid at room temperature. The entire molecule is approximately planar with a maximum deviation of 0.047 (2) Å. An intramolecular C—H⋯O interaction is observed. O—H⋯Cl, N—H⋯Cl, N—H⋯O, N—H⋯N, C—H⋯Cl and C—H⋯O hydrogen-bonds stabilize the crystal structure.

Related literature

Schiff bases have been used extensively as ligands in the field of coordination chemistry, see: Cui et al. (2005 ). For their antimicrobial and anticancer applications, see: Tarafder et al. (2000 ) and Deschamps et al. (2003 ), respectively.

Experimental

Crystal data

C₁₂H₁₂N₃O₂⁺·Cl⁻·H₂O
M_r = 283.71
Monoclinic, P 2₁ /c
a = 8.5258 (17) Å
b = 14.435 (3) Å
c = 13.625 (4) Å
β = 123.55 (2)°
V = 1397.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.11 mm

Data collection

Bruker P4 diffractometer
Absorption correction: none
13328 measured reflections
3187 independent reflections
2715 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.107
S = 1.07
3187 reflections
180 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯Cl1ⁱ	0.86 (3)	2.40 (3)	3.229 (3)	162 (3)
O1W—H1W1⋯Cl1ⁱⁱ	0.72 (3)	2.51 (3)	3.225 (3)	177 (2)
N2—H2A⋯Cl1ⁱ	0.86	2.39	3.2243 (15)	164
N3—H3A⋯O2ⁱⁱ	0.86	1.89	2.639 (2)	144
N3—H3A⋯N1ⁱⁱ	0.86	2.50	3.2238 (18)	142
C3—H3B⋯Cl1ⁱⁱⁱ	0.93	2.76	3.6574 (19)	162
C6—H6A⋯Cl1ⁱ	0.93	2.69	3.5374 (18)	151
C9—H9A⋯Cl1ⁱ	0.93	2.64	3.5656 (18)	171
C11—H11A⋯O1ⁱⁱ	0.93	2.45	3.1694 (19)	135
C12—H12A⋯O2	0.93	2.39	2.713 (2)	100
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028426/at2845sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028426/at2845Isup2.hkl

checkCIF report

Comment top

Schiff bases have been used extensively as ligands in the field of coordination chemistry (Cui et al., 2005). And they have antimicrobial (Tarafder et al., 2000) and anticancer applications (Deschamps et al., 2003). The title compound (I) was synthesized and we report its crystal structure here.

In the crystal structure of (I) (Fig. 1), the carbon and nitrogen atoms are nearly the same plane with a maximum deviation of 0.047Å for N2. There are intra- and intermolecular O—H···Cl, N—H···Cl, N—H···O, N—H···N, C—H···Cl and C—H···O hydrogen-bonds to stabilize the crystal structure (Table 1).

Related literature top

Schiff bases have been used extensively as ligands in the field of coordination chemistry, see: Cui et al. (2005). For their antimicrobial and anticancer applications, see: Tarafder et al. (2000) and Deschamps et al. (2003), respectively.

Experimental top

A mixture of N'-[(5-methyl-2-furyl)methylene]isonicotinohydrazide (0.02 mol) and hydrochloric acid (0.01 mol) was stirred with ethanol (50 ml) at 298 K for 2 h, then afford the title compound (2.61 g, yield 92%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and trichloromethane (1:1) at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008.

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

4-{[(5-Methyl-2-furyl)methylene]hydrazinocarbonyl}pyridinium chloride monohydrate top

Crystal data top

C₁₂H₁₂N₃O₂⁺·Cl⁻·H₂O	F(000) = 592
M_r = 283.71	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2715 reflections
a = 8.5258 (17) Å	θ = 3.1–27.5°
b = 14.435 (3) Å	µ = 0.28 mm⁻¹
c = 13.625 (4) Å	T = 293 K
β = 123.55 (2)°	Bar, yellow
V = 1397.5 (7) Å³	0.20 × 0.15 × 0.11 mm
Z = 4

Data collection top

Bruker P4 diffractometer	2715 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
Detector resolution: 3 pixels mm^-1	h = −10→11
ω scans	k = −18→18
13328 measured reflections	l = −17→17
3187 independent reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0543P)² + 0.3029P] where P = (F_o² + 2F_c²)/3
3187 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₂H₁₂N₃O₂⁺·Cl⁻·H₂O	V = 1397.5 (7) Å³
M_r = 283.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5258 (17) Å	µ = 0.28 mm⁻¹
b = 14.435 (3) Å	T = 293 K
c = 13.625 (4) Å	0.20 × 0.15 × 0.11 mm
β = 123.55 (2)°

Data collection top

Bruker P4 diffractometer	2715 reflections with I > 2σ(I)
13328 measured reflections	R_int = 0.026
3187 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.27 e Å⁻³
3187 reflections	Δρ_min = −0.21 e Å⁻³
180 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
Cl1	0.22892 (6)	−0.42533 (3)	−0.18006 (4)	0.06023 (16)
O1	0.51022 (13)	0.04123 (6)	0.13453 (8)	0.0380 (2)
O2	0.05971 (14)	−0.22008 (7)	−0.02944 (10)	0.0536 (3)
N1	0.16922 (14)	−0.04732 (7)	−0.03026 (9)	0.0327 (2)
N2	−0.00554 (14)	−0.08118 (7)	−0.11953 (9)	0.0327 (2)
H2A	−0.0844	−0.0467	−0.1778	0.039*
N3	−0.57485 (15)	−0.28167 (8)	−0.36865 (9)	0.0392 (3)
H3A	−0.6822	−0.3057	−0.4198	0.047*
C1	0.8247 (2)	0.07121 (14)	0.30399 (16)	0.0616 (5)
H1B	0.9141	0.1209	0.3397	0.092*
H1C	0.8779	0.0215	0.2847	0.092*
H1D	0.7941	0.0493	0.3580	0.092*
C2	0.65193 (19)	0.10503 (11)	0.19547 (13)	0.0419 (3)
C3	0.5985 (2)	0.18739 (10)	0.14057 (14)	0.0469 (4)
H3B	0.6695	0.2415	0.1641	0.056*
C4	0.4137 (2)	0.17617 (10)	0.04032 (13)	0.0441 (3)
H4A	0.3395	0.2216	−0.0145	0.053*
C5	0.36538 (19)	0.08648 (9)	0.03927 (12)	0.0354 (3)
C6	0.19437 (19)	0.03842 (9)	−0.04240 (11)	0.0359 (3)
H6A	0.0978	0.0707	−0.1067	0.043*
C7	−0.04668 (16)	−0.16914 (9)	−0.11160 (10)	0.0321 (3)
C8	−0.23608 (16)	−0.20547 (8)	−0.20798 (10)	0.0301 (3)
C9	−0.37266 (17)	−0.15335 (9)	−0.30253 (11)	0.0365 (3)
H9A	−0.3495	−0.0920	−0.3115	0.044*
C10	−0.54274 (18)	−0.19394 (10)	−0.38265 (11)	0.0404 (3)
H10A	−0.6356	−0.1601	−0.4468	0.049*
C11	−0.4484 (2)	−0.33342 (10)	−0.27924 (13)	0.0441 (3)
H11A	−0.4768	−0.3942	−0.2721	0.053*
C12	−0.27438 (19)	−0.29683 (9)	−0.19686 (12)	0.0413 (3)
H12A	−0.1837	−0.3330	−0.1346	0.050*
O1W	−0.3179 (3)	−0.06393 (18)	−0.5308 (2)	0.1060 (7)
H2W1	−0.282 (4)	−0.0189 (19)	−0.481 (2)	0.093 (8)*
H1W1	−0.419 (4)	−0.0676 (18)	−0.566 (2)	0.084 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0599 (3)	0.0341 (2)	0.0513 (2)	−0.00819 (16)	0.00847 (19)	−0.00564 (15)
O1	0.0337 (5)	0.0317 (5)	0.0423 (5)	−0.0068 (4)	0.0170 (4)	−0.0055 (4)
O2	0.0291 (5)	0.0402 (5)	0.0497 (6)	−0.0051 (4)	−0.0044 (4)	0.0125 (5)
N1	0.0253 (5)	0.0331 (5)	0.0312 (5)	−0.0053 (4)	0.0104 (4)	−0.0060 (4)
N2	0.0240 (5)	0.0305 (5)	0.0292 (5)	−0.0022 (4)	0.0056 (4)	−0.0012 (4)
N3	0.0252 (5)	0.0466 (7)	0.0317 (5)	−0.0085 (5)	0.0070 (4)	−0.0110 (5)
C1	0.0368 (8)	0.0758 (12)	0.0565 (10)	−0.0073 (8)	0.0159 (7)	−0.0122 (9)
C2	0.0348 (6)	0.0454 (7)	0.0472 (8)	−0.0143 (6)	0.0236 (6)	−0.0167 (6)
C3	0.0515 (8)	0.0396 (7)	0.0572 (9)	−0.0204 (7)	0.0348 (7)	−0.0155 (7)
C4	0.0531 (8)	0.0334 (7)	0.0484 (8)	−0.0089 (6)	0.0297 (7)	−0.0025 (6)
C5	0.0377 (7)	0.0321 (6)	0.0359 (6)	−0.0053 (5)	0.0200 (6)	−0.0047 (5)
C6	0.0348 (6)	0.0332 (6)	0.0335 (6)	−0.0030 (5)	0.0151 (5)	−0.0032 (5)
C7	0.0221 (5)	0.0321 (6)	0.0305 (6)	−0.0002 (5)	0.0072 (5)	−0.0007 (5)
C8	0.0217 (5)	0.0319 (6)	0.0282 (5)	−0.0003 (5)	0.0084 (5)	−0.0021 (5)
C9	0.0278 (6)	0.0365 (6)	0.0326 (6)	−0.0007 (5)	0.0089 (5)	0.0038 (5)
C10	0.0262 (6)	0.0476 (8)	0.0302 (6)	0.0008 (6)	0.0047 (5)	0.0022 (5)
C11	0.0386 (7)	0.0333 (7)	0.0435 (7)	−0.0094 (6)	0.0120 (6)	−0.0066 (6)
C12	0.0319 (6)	0.0307 (6)	0.0384 (7)	−0.0011 (5)	0.0050 (5)	0.0010 (5)
O1W	0.0743 (12)	0.152 (2)	0.0905 (13)	−0.0102 (12)	0.0446 (11)	−0.0516 (13)

Geometric parameters (Å, º) top

O1—C5	1.3655 (17)	C3—H3B	0.9300
O1—C2	1.3742 (16)	C4—C5	1.3566 (19)
O2—C7	1.2225 (16)	C4—H4A	0.9300
N1—C6	1.2823 (17)	C5—C6	1.4324 (18)
N1—N2	1.3911 (14)	C6—H6A	0.9300
N2—C7	1.3375 (16)	C7—C8	1.5044 (16)
N2—H2A	0.8600	C8—C12	1.3868 (18)
N3—C11	1.3239 (18)	C8—C9	1.3869 (17)
N3—C10	1.3314 (19)	C9—C10	1.3741 (18)
N3—H3A	0.8600	C9—H9A	0.9300
C1—C2	1.479 (2)	C10—H10A	0.9300
C1—H1B	0.9600	C11—C12	1.3780 (18)
C1—H1C	0.9600	C11—H11A	0.9300
C1—H1D	0.9600	C12—H12A	0.9300
C2—C3	1.343 (2)	O1W—H2W1	0.87 (3)
C3—C4	1.412 (2)	O1W—H1W1	0.72 (3)

C5—O1—C2	106.56 (11)	C4—C5—C6	130.05 (13)
C6—N1—N2	113.64 (11)	O1—C5—C6	120.28 (11)
C7—N2—N1	117.70 (10)	N1—C6—C5	122.56 (12)
C7—N2—H2A	121.1	N1—C6—H6A	118.7
N1—N2—H2A	121.1	C5—C6—H6A	118.7
C11—N3—C10	122.76 (11)	O2—C7—N2	123.37 (11)
C11—N3—H3A	118.6	O2—C7—C8	119.01 (11)
C10—N3—H3A	118.6	N2—C7—C8	117.61 (10)
C2—C1—H1B	109.5	C12—C8—C9	119.33 (11)
C2—C1—H1C	109.5	C12—C8—C7	116.11 (11)
H1B—C1—H1C	109.5	C9—C8—C7	124.53 (11)
C2—C1—H1D	109.5	C10—C9—C8	118.83 (13)
H1B—C1—H1D	109.5	C10—C9—H9A	120.6
H1C—C1—H1D	109.5	C8—C9—H9A	120.6
C3—C2—O1	110.02 (13)	N3—C10—C9	120.13 (12)
C3—C2—C1	133.87 (14)	N3—C10—H10A	119.9
O1—C2—C1	116.11 (14)	C9—C10—H10A	119.9
C2—C3—C4	106.92 (13)	N3—C11—C12	119.73 (13)
C2—C3—H3B	126.5	N3—C11—H11A	120.1
C4—C3—H3B	126.5	C12—C11—H11A	120.1
C5—C4—C3	106.83 (14)	C11—C12—C8	119.21 (12)
C5—C4—H4A	126.6	C11—C12—H12A	120.4
C3—C4—H4A	126.6	C8—C12—H12A	120.4
C4—C5—O1	109.67 (12)	H2W1—O1W—H1W1	111 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···Cl1ⁱ	0.86 (3)	2.40 (3)	3.229 (3)	162 (3)
O1W—H1W1···Cl1ⁱⁱ	0.72 (3)	2.51 (3)	3.225 (3)	177 (2)
N2—H2A···Cl1ⁱ	0.86	2.39	3.2243 (15)	164
N3—H3A···O2ⁱⁱ	0.86	1.89	2.639 (2)	144
N3—H3A···N1ⁱⁱ	0.86	2.50	3.2238 (18)	142
C3—H3B···Cl1ⁱⁱⁱ	0.93	2.76	3.6574 (19)	162
C6—H6A···Cl1ⁱ	0.93	2.69	3.5374 (18)	151
C9—H9A···Cl1ⁱ	0.93	2.64	3.5656 (18)	171
C11—H11A···O1ⁱⁱ	0.93	2.45	3.1694 (19)	135
C12—H12A···O2	0.93	2.39	2.713 (2)	100

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₃O₂⁺·Cl⁻·H₂O
M_r	283.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.5258 (17), 14.435 (3), 13.625 (4)
β (°)	123.55 (2)
V (Å³)	1397.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.20 × 0.15 × 0.11

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13328, 3187, 2715
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.107, 1.07
No. of reflections	3187
No. of parameters	180
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···Cl1ⁱ	0.86 (3)	2.40 (3)	3.229 (3)	162 (3)
O1W—H1W1···Cl1ⁱⁱ	0.72 (3)	2.51 (3)	3.225 (3)	177 (2)
N2—H2A···Cl1ⁱ	0.8600	2.3900	3.2243 (15)	164.00
N3—H3A···O2ⁱⁱ	0.8600	1.8900	2.639 (2)	144.00
N3—H3A···N1ⁱⁱ	0.8600	2.5000	3.2238 (18)	142.00
C3—H3B···Cl1ⁱⁱⁱ	0.9300	2.7600	3.6574 (19)	162.00
C6—H6A···Cl1ⁱ	0.9300	2.6900	3.5374 (18)	151.00
C9—H9A···Cl1ⁱ	0.9300	2.6400	3.5656 (18)	171.00
C11—H11A···O1ⁱⁱ	0.9300	2.4500	3.1694 (19)	135.00
C12—H12A···O2	0.9300	2.3900	2.713 (2)	100.00

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

Acknowledgements

The authors would like to thank the Natural Science Foundation of Shandong Province (No.Y2008B30).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cui, S.-L., Zhou, F.-Y. & Lin, X.-F. (2005). Acta Cryst. E61, o3198–o3199. Web of Science CSD CrossRef IUCr Journals Google Scholar
Deschamps, P., Kulkarni, P. P. & Sarkar, B. (2003). Inorg. Chem. 42, 7366–7368. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tarafder, M. T. H., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456–460. Web of Science CrossRef CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-{[(5-Methyl-2-fur­yl)methyl­ene]hydrazinocarbon­yl}pyridinium chloride monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-{[(5-Methyl-2-furyl)methylene]hydrazinocarbonyl}pyridinium chloride monohydrate