4-{[(5-Methyl-2-fur-yl)methyl-ene]hydrazinocarbon-yl}pyridinium chloride monohydrate.

The title compound, C(12)H(12)N(3)O(2) (+)·Cl(-)·H(2)O, was prepared by the reaction of N'-[(5-methyl-2-fur-yl)methyl-ene]isonicotino-hydrazide and hydro-chloric 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 = 283.71

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.07

3187 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H12N3O2+·Cl−·H2O	F(000) = 592
Mr = 283.71	Dx = 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

Bruker P4 diffractometer	2715 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 27.5°, θmin = 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 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(Fo2) + (0.0543P)2 + 0.3029P] where P = (Fo2 + 2Fc2)/3
3187 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) ; (iii) .