Crystal structure of (E)-3-{[2-(2,4-di­chloro­benzyl­idene)hydrazin-1-yl]carbon­yl}pyridinium chloride trihydrate

Novina, J.J.; Vasuki, G.; Suresh, M.; Padusha, M.S.A.

doi:10.1107/S2056989015000286

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o105-o106

doi:10.1107/S2056989015000286

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Crystal structure of (E)-3-{[2-(2,4-dichlorobenzylidene)hydrazin-1-yl]carbonyl}pyridinium chloride trihydrate

J. Josephine Novina,^a G. Vasuki,^b ^* M. Suresh ^c and M. Syed Ali Padusha ^c

^aDepartment of Physics, Idhaya College for Women, Kumbakonam 1, India, ^bDepartment of Physics, Kunthavai Naachiar Govt. Arts College (W) (Autonomous), Thanjavur 7, India, and ^cPG & Research Department of Chemistry, Jamal Mohamed College, Tiruchirappalli 20, India
^*Correspondence e-mail: vasuki.arasi@yahoo.com

Edited by O. Büyükgüngör, Ondokuz Mayıs University, Turkey (Received 31 December 2014; accepted 7 January 2015; online 10 January 2015)

In the title hydrated salt, C₁₃H₁₀Cl₂N₃O⁺·Cl⁻·3H₂O, the organic cation exhibits a dihedral angle of 8.26 (14)° between the mean planes of the pyridinium and benzene rings, and dihedral angles of 8.70 (15) and 15.93 (5)° between the mean planes of the hydrazide group and the benzene and pyridinium rings, respectively. In the crystal, N—H⋯O, N—H⋯Cl, C—H⋯O, C—H⋯Cl, O—H⋯O, O—H⋯N and O—H⋯Cl hydrogen bonds link the complex cations, chloride anions and solvent water molecules into a three-dimensional network.

Keywords: crystals structure; pyridinium; hydrazide group; hydrogen bonds.

CCDC reference: 1028701

1. Related literature

For the biological activity of hydrazones, see: Kaplancikli et al. (2012 ); Babahan et al. (2013 ). For related structures, see: Novina et al. (2013 , 2014 ).

2. Experimental

2.1. Crystal data

C₁₃H₁₀Cl₂N₃O⁺·Cl⁻·3H₂O
M_r = 384.64
Triclinic, $[P \overline 1]$
a = 8.4631 (4) Å
b = 9.5968 (5) Å
c = 10.8300 (6) Å
α = 76.604 (2)°
β = 89.155 (2)°
γ = 83.195 (2)°
V = 849.56 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.875, T_max = 0.908
6548 measured reflections
4037 independent reflections
3007 reflections with I > 2σ(I)
R_int = 0.019

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.124
S = 1.04
4037 reflections
234 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1Wⁱ	0.88 (2)	1.77 (2)	2.646 (2)	176 (3)
N2—H2N⋯Cl2	0.86 (2)	2.40 (2)	3.2432 (19)	168 (2)
C1—H1⋯O1ⁱⁱ	0.93	2.40	3.214 (3)	146
C3—H3⋯Cl2ⁱⁱⁱ	0.93	2.79	3.608 (2)	147
C7—H7⋯Cl2	0.93	2.76	3.588 (2)	149
O1W—H1WA⋯O2W	0.77 (2)	1.97 (2)	2.711 (3)	163 (3)
O1W—H1WB⋯O1^iv	0.81 (2)	2.12 (2)	2.826 (2)	146 (3)
O1W—H1WB⋯N3^iv	0.81 (2)	2.53 (2)	3.218 (2)	143 (3)
O2W—H2WA⋯Cl2ⁱⁱⁱ	0.83 (2)	2.36 (2)	3.190 (2)	177 (3)
O2W—H2WB⋯Cl2^v	0.81 (2)	2.42 (2)	3.214 (2)	169 (3)
O3W—H3WA⋯Cl2	0.93 (2)	2.28 (2)	3.206 (3)	174 (3)
O3W—H3WB⋯O1W^vi	0.90 (2)	2.25 (2)	3.146 (4)	177 (3)
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1; (v) x, y+1, z; (vi) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1028701

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989015000286/bq2398sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015000286/bq2398Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015000286/bq2398Isup3.cml

checkCIF report

Structural commentary top

Hydrozones have received considerable attention due to their biological importance in medicinal chemistry. Many studies have confirmed that hydrazone derivatives exhibit a wide spectrum of biological effects including anti-inflammatory activity (Kaplancikli et al., 2012). Moreover, the hydrazone group plays an important role of the antimicrobial and possesses interesting antibacterial, antifungal and anti-tubercular activities (Babahan et al., 2013). As part of our studies on hydrazone derivatives (Novina et al., 2013; 2014), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound, illustrated in Fig. 1, consists of one organic cation, one Cl^- anion and three water molecules. The hydrazone molecule adopts an E–configuration with respect to the N3═C7 bond with the torsion angle of N2—N3—C7—C8 = -178.81 (18)°. Phenyl and pyridine rings (C8—C13 and C1/N1/C2—C5, respectively) are each planar with a dihedral angle of 8.26 (14)° between their mean-planes. The mean plane through the hydrazide unit (N3/N2/C6/O1) forms dihedral angle of 8.70 (15) and 15.93 (5)°, respectively, with the phenyl and pyridinium rings. The two chlorine atoms are in anti–periplanar positions with respect to the phenyl rings to which they are attached.

In the crystal, the organic cation, the chloride anion and the three water molecules of crystallization are linked through an intricate hydrogen-bonding network consisting of N—H···O, N—H···Cl, C—H···O, C—H···Cl, O—H···O, O—H···N and O—H···Cl interactions that consolidate a three–dimensional network (Table 1). One of the H atoms of the water molecule (O1W) forms bifurcated hydrogen bonds to the azomethine nitrogen and the carbonyl oxygen atoms of one neighbouring molecule and the same water molecule acts as a hydrogen bond acceptor towards another hydrazone molecule through N–H···O hydrogen bonds (Fig. 2). Further molecules are linked via a pair of C—H···O hydrogen bonds forming inversion dimers with an R²₂(10) ring motif (Fig. 3). The crystal structure is further stabilized by N—H···Cl, C—H···Cl and O—H···Cl hydrogen bonds.

Synthesis and crystallization top

2,4-dichlorobenzaldehyde (0.175 g, 0.001 mol) was added to an aqueous solution of nicotinicacid hydrazide (0.34 g, 0.001 mol), followed by 2 drops of concentrated HCl is added. After the addition was complete, the reaction mixture was stirred well at room temperature for 1 h. The colourless solid that formed was filtered, dried and washed with petroleum ether (40–60%). The crude solid obtained was dried and recrystallized from absolute alcohol. The recrystallized product was dried over vacuum. [m.pt: 411–413 K; yield:92%].

Refinement top

The H atoms of the solvent water were located in a difference map and refined freely. All Other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.93 Å, N—H = 0.86–0.88 Å and with U_iso(H) = 1.2U_eq(CH).

Related literature top

For the biological activity of hydrazones, see: Kaplancikli et al. (2012); Babahan et al. (2013). For related structures, see: Novina et al. (2013, 2014).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.
	Fig. 3. Part of the crystal packing of the title compound, showing the formation of R₂²(10) motif. The Cl^- and the water molecules are omitted for the sake of clarity.

(E)-3-{[2-(2,4-Dichlorobenzylidene)hydrazin-1-yl]carbonyl}pyridinium chloride trihydrate top

Crystal data top

C₁₃H₁₀Cl₂N₃O⁺·Cl⁻·3H₂O	Z = 2
M_r = 384.64	F(000) = 396
Triclinic, P1	D_x = 1.504 Mg m⁻³
a = 8.4631 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5968 (5) Å	Cell parameters from 6548 reflections
c = 10.8300 (6) Å	θ = 1.0–28.2°
α = 76.604 (2)°	µ = 0.56 mm⁻¹
β = 89.155 (2)°	T = 293 K
γ = 83.195 (2)°	Block, colorless
V = 849.56 (8) Å³	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4037 independent reflections
Radiation source: fine-focus sealed tube	3007 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω and ϕ scan	θ_max = 28.2°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
T_min = 0.875, T_max = 0.908	k = −9→12
6548 measured reflections	l = −8→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0621P)² + 0.184P] where P = (F_o² + 2F_c²)/3
4037 reflections	(Δ/σ)_max < 0.001
234 parameters	Δρ_max = 0.28 e Å⁻³
8 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₃H₁₀Cl₂N₃O⁺·Cl⁻·3H₂O	γ = 83.195 (2)°
M_r = 384.64	V = 849.56 (8) Å³
Triclinic, P1	Z = 2
a = 8.4631 (4) Å	Mo Kα radiation
b = 9.5968 (5) Å	µ = 0.56 mm⁻¹
c = 10.8300 (6) Å	T = 293 K
α = 76.604 (2)°	0.35 × 0.30 × 0.25 mm
β = 89.155 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4037 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3007 reflections with I > 2σ(I)
T_min = 0.875, T_max = 0.908	R_int = 0.019
6548 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	8 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.28 e Å⁻³
4037 reflections	Δρ_min = −0.37 e Å⁻³
234 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	0.52954 (7)	−0.24772 (6)	0.38718 (6)	0.04957 (17)
Cl3	0.72649 (9)	−0.56838 (6)	0.84324 (7)	0.0656 (2)
O1	0.8879 (2)	0.32962 (16)	0.49886 (15)	0.0485 (4)
N1	0.8808 (2)	0.69456 (19)	0.21816 (19)	0.0445 (4)
N2	0.7666 (2)	0.21144 (17)	0.37617 (17)	0.0372 (4)
N3	0.7793 (2)	0.08783 (17)	0.47208 (16)	0.0367 (4)
C1	0.8932 (2)	0.5703 (2)	0.3054 (2)	0.0386 (5)
H1	0.9622	0.5563	0.3744	0.046*
C2	0.7810 (3)	0.7223 (2)	0.1195 (2)	0.0491 (6)
H2	0.7734	0.8112	0.0617	0.059*
C3	0.6892 (3)	0.6188 (3)	0.1031 (2)	0.0501 (6)
H3	0.6191	0.6371	0.0344	0.060*
C4	0.7022 (3)	0.4873 (2)	0.1899 (2)	0.0421 (5)
H4	0.6426	0.4157	0.1785	0.050*
C5	0.8039 (2)	0.4620 (2)	0.29380 (19)	0.0340 (4)
C6	0.8238 (2)	0.3282 (2)	0.39897 (19)	0.0343 (4)
C7	0.7166 (3)	−0.0174 (2)	0.4476 (2)	0.0392 (5)
H7	0.6685	−0.0079	0.3690	0.047*
C8	0.7204 (2)	−0.1530 (2)	0.5436 (2)	0.0364 (4)
C9	0.8056 (3)	−0.1751 (2)	0.6573 (2)	0.0423 (5)
H9	0.8619	−0.1024	0.6711	0.051*
C10	0.8088 (3)	−0.3016 (2)	0.7499 (2)	0.0450 (5)
H10	0.8654	−0.3141	0.8254	0.054*
C11	0.7259 (3)	−0.4091 (2)	0.7274 (2)	0.0436 (5)
C12	0.6423 (3)	−0.3936 (2)	0.6166 (2)	0.0439 (5)
H12	0.5886	−0.4679	0.6028	0.053*
C13	0.6391 (2)	−0.2655 (2)	0.5254 (2)	0.0373 (4)
Cl2	0.59217 (8)	0.15917 (7)	0.12886 (6)	0.05501 (18)
O1W	0.0683 (2)	0.87717 (19)	0.26788 (17)	0.0547 (4)
O2W	0.3189 (3)	0.9558 (3)	0.1201 (2)	0.0859 (7)
O3W	0.9617 (3)	0.1595 (4)	0.0595 (4)	0.1333 (13)
H1N	0.947 (3)	0.753 (3)	0.234 (3)	0.066 (8)*
H2N	0.725 (3)	0.210 (3)	0.3047 (18)	0.051 (7)*
H1WA	0.145 (3)	0.882 (4)	0.230 (3)	0.076*
H1WB	0.088 (4)	0.849 (3)	0.3430 (18)	0.076*
H2WA	0.344 (4)	0.923 (3)	0.057 (2)	0.076*
H2WB	0.389 (3)	1.001 (3)	0.133 (3)	0.076*
H3WA	0.853 (2)	0.161 (3)	0.074 (3)	0.076*
H3WB	0.991 (4)	0.077 (2)	0.117 (3)	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0565 (3)	0.0471 (3)	0.0514 (3)	−0.0168 (2)	−0.0045 (3)	−0.0186 (2)
Cl3	0.0796 (4)	0.0369 (3)	0.0704 (4)	−0.0098 (3)	0.0025 (3)	0.0091 (3)
O1	0.0700 (10)	0.0389 (8)	0.0384 (8)	−0.0215 (7)	−0.0140 (7)	−0.0039 (6)
N1	0.0479 (10)	0.0351 (9)	0.0495 (11)	−0.0170 (8)	−0.0014 (9)	−0.0017 (8)
N2	0.0479 (10)	0.0294 (8)	0.0344 (9)	−0.0117 (7)	−0.0069 (8)	−0.0040 (7)
N3	0.0443 (9)	0.0282 (8)	0.0368 (9)	−0.0086 (7)	−0.0015 (7)	−0.0039 (7)
C1	0.0400 (10)	0.0347 (10)	0.0411 (11)	−0.0117 (8)	−0.0036 (9)	−0.0047 (9)
C2	0.0593 (14)	0.0387 (11)	0.0442 (12)	−0.0108 (10)	−0.0020 (11)	0.0034 (10)
C3	0.0572 (13)	0.0476 (12)	0.0412 (12)	−0.0078 (10)	−0.0140 (10)	0.0001 (10)
C4	0.0476 (12)	0.0382 (10)	0.0414 (11)	−0.0117 (9)	−0.0078 (9)	−0.0073 (9)
C5	0.0379 (10)	0.0297 (9)	0.0352 (10)	−0.0089 (8)	−0.0017 (8)	−0.0065 (8)
C6	0.0383 (10)	0.0304 (9)	0.0347 (10)	−0.0094 (8)	−0.0026 (8)	−0.0059 (8)
C7	0.0491 (11)	0.0307 (10)	0.0395 (11)	−0.0106 (8)	−0.0033 (9)	−0.0085 (8)
C8	0.0415 (10)	0.0280 (9)	0.0414 (11)	−0.0071 (8)	0.0027 (9)	−0.0098 (8)
C9	0.0498 (12)	0.0315 (10)	0.0479 (12)	−0.0115 (9)	−0.0007 (10)	−0.0103 (9)
C10	0.0505 (12)	0.0389 (11)	0.0446 (12)	−0.0062 (9)	−0.0015 (10)	−0.0071 (9)
C11	0.0498 (12)	0.0268 (9)	0.0509 (13)	−0.0043 (9)	0.0075 (10)	−0.0027 (9)
C12	0.0501 (12)	0.0295 (10)	0.0557 (14)	−0.0133 (9)	0.0073 (10)	−0.0133 (9)
C13	0.0407 (10)	0.0320 (10)	0.0427 (11)	−0.0084 (8)	0.0028 (9)	−0.0141 (9)
Cl2	0.0667 (4)	0.0567 (4)	0.0458 (3)	−0.0209 (3)	−0.0107 (3)	−0.0128 (3)
O1W	0.0705 (12)	0.0484 (9)	0.0457 (10)	−0.0255 (9)	−0.0100 (9)	−0.0022 (8)
O2W	0.1004 (17)	0.1131 (19)	0.0687 (14)	−0.0676 (15)	0.0228 (12)	−0.0443 (13)
O3W	0.0783 (17)	0.141 (3)	0.150 (3)	−0.0212 (18)	−0.0129 (18)	0.034 (2)

Geometric parameters (Å, º) top

Cl1—C13	1.736 (2)	C5—C6	1.501 (3)
Cl3—C11	1.738 (2)	C7—C8	1.463 (3)
O1—C6	1.221 (2)	C7—H7	0.9300
N1—C2	1.330 (3)	C8—C9	1.397 (3)
N1—C1	1.333 (3)	C8—C13	1.398 (3)
N1—H1N	0.882 (17)	C9—C10	1.382 (3)
N2—C6	1.346 (2)	C9—H9	0.9300
N2—N3	1.378 (2)	C10—C11	1.382 (3)
N2—H2N	0.856 (16)	C10—H10	0.9300
N3—C7	1.275 (2)	C11—C12	1.371 (3)
C1—C5	1.385 (3)	C12—C13	1.384 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.374 (3)	O1W—H1WA	0.766 (17)
C2—H2	0.9300	O1W—H1WB	0.809 (18)
C3—C4	1.381 (3)	O2W—H2WA	0.829 (17)
C3—H3	0.9300	O2W—H2WB	0.805 (17)
C4—C5	1.385 (3)	O3W—H3WA	0.930 (17)
C4—H4	0.9300	O3W—H3WB	0.897 (17)

C2—N1—C1	122.53 (18)	N3—C7—C8	119.86 (19)
C2—N1—H1N	125.4 (19)	N3—C7—H7	120.1
C1—N1—H1N	112.1 (19)	C8—C7—H7	120.1
C6—N2—N3	117.78 (17)	C9—C8—C13	117.38 (18)
C6—N2—H2N	123.2 (16)	C9—C8—C7	121.09 (18)
N3—N2—H2N	119.0 (16)	C13—C8—C7	121.53 (19)
C7—N3—N2	115.19 (18)	C10—C9—C8	121.99 (19)
N1—C1—C5	120.32 (19)	C10—C9—H9	119.0
N1—C1—H1	119.8	C8—C9—H9	119.0
C5—C1—H1	119.8	C11—C10—C9	118.3 (2)
N1—C2—C3	119.7 (2)	C11—C10—H10	120.9
N1—C2—H2	120.1	C9—C10—H10	120.9
C3—C2—H2	120.1	C12—C11—C10	121.94 (19)
C2—C3—C4	119.3 (2)	C12—C11—Cl3	118.97 (16)
C2—C3—H3	120.3	C10—C11—Cl3	119.09 (19)
C4—C3—H3	120.3	C11—C12—C13	118.96 (19)
C3—C4—C5	120.05 (19)	C11—C12—H12	120.5
C3—C4—H4	120.0	C13—C12—H12	120.5
C5—C4—H4	120.0	C12—C13—C8	121.4 (2)
C1—C5—C4	118.05 (18)	C12—C13—Cl1	117.93 (15)
C1—C5—C6	115.94 (17)	C8—C13—Cl1	120.64 (16)
C4—C5—C6	125.98 (17)	H1WA—O1W—H1WB	110 (3)
O1—C6—N2	123.58 (18)	H2WA—O2W—H2WB	108 (3)
O1—C6—C5	120.06 (17)	H3WA—O3W—H3WB	96 (3)
N2—C6—C5	116.35 (17)

C6—N2—N3—C7	176.82 (19)	N3—C7—C8—C9	−6.6 (3)
C2—N1—C1—C5	1.9 (3)	N3—C7—C8—C13	173.4 (2)
C1—N1—C2—C3	−1.8 (4)	C13—C8—C9—C10	−0.9 (3)
N1—C2—C3—C4	0.0 (4)	C7—C8—C9—C10	179.1 (2)
C2—C3—C4—C5	1.6 (4)	C8—C9—C10—C11	0.6 (3)
N1—C1—C5—C4	−0.2 (3)	C9—C10—C11—C12	0.3 (3)
N1—C1—C5—C6	−178.47 (19)	C9—C10—C11—Cl3	−179.30 (18)
C3—C4—C5—C1	−1.6 (3)	C10—C11—C12—C13	−1.0 (3)
C3—C4—C5—C6	176.5 (2)	Cl3—C11—C12—C13	178.67 (16)
N3—N2—C6—O1	1.0 (3)	C11—C12—C13—C8	0.7 (3)
N3—N2—C6—C5	−178.36 (17)	C11—C12—C13—Cl1	−178.90 (17)
C1—C5—C6—O1	14.8 (3)	C9—C8—C13—C12	0.3 (3)
C4—C5—C6—O1	−163.3 (2)	C7—C8—C13—C12	−179.7 (2)
C1—C5—C6—N2	−165.78 (19)	C9—C8—C13—Cl1	179.82 (16)
C4—C5—C6—N2	16.1 (3)	C7—C8—C13—Cl1	−0.2 (3)
N2—N3—C7—C8	−178.81 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1Wⁱ	0.88 (2)	1.77 (2)	2.646 (2)	176 (3)
N2—H2N···Cl2	0.86 (2)	2.40 (2)	3.2432 (19)	168 (2)
C1—H1···O1ⁱⁱ	0.93	2.40	3.214 (3)	146
C3—H3···Cl2ⁱⁱⁱ	0.93	2.79	3.608 (2)	147
C7—H7···Cl2	0.93	2.76	3.588 (2)	149
O1W—H1WA···O2W	0.77 (2)	1.97 (2)	2.711 (3)	163 (3)
O1W—H1WB···O1^iv	0.81 (2)	2.12 (2)	2.826 (2)	146 (3)
O1W—H1WB···N3^iv	0.81 (2)	2.53 (2)	3.218 (2)	143 (3)
O2W—H2WA···Cl2ⁱⁱⁱ	0.83 (2)	2.36 (2)	3.190 (2)	177 (3)
O2W—H2WB···Cl2^v	0.81 (2)	2.42 (2)	3.214 (2)	169 (3)
O3W—H3WA···Cl2	0.93 (2)	2.28 (2)	3.206 (3)	174 (3)
O3W—H3WB···O1W^vi	0.90 (2)	2.25 (2)	3.146 (4)	177 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1Wⁱ	0.882 (17)	1.765 (18)	2.646 (2)	176 (3)
N2—H2N···Cl2	0.856 (16)	2.401 (17)	3.2432 (19)	168 (2)
C1—H1···O1ⁱⁱ	0.93	2.40	3.214 (3)	145.8
C3—H3···Cl2ⁱⁱⁱ	0.93	2.79	3.608 (2)	146.7
C7—H7···Cl2	0.93	2.76	3.588 (2)	148.6
O1W—H1WA···O2W	0.766 (17)	1.97 (2)	2.711 (3)	163 (3)
O1W—H1WB···O1^iv	0.809 (18)	2.12 (2)	2.826 (2)	146 (3)
O1W—H1WB···N3^iv	0.809 (18)	2.53 (2)	3.218 (2)	143 (3)
O2W—H2WA···Cl2ⁱⁱⁱ	0.829 (17)	2.363 (18)	3.190 (2)	177 (3)
O2W—H2WB···Cl2^v	0.805 (17)	2.420 (18)	3.214 (2)	169 (3)
O3W—H3WA···Cl2	0.930 (17)	2.279 (18)	3.206 (3)	174 (3)
O3W—H3WB···O1W^vi	0.897 (17)	2.250 (19)	3.146 (4)	177 (3)

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

Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, STIC, Cochin University of Science & Technology, Cochin, for the single-crystal X-ray data collection.

References

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Volume 71| Part 2| February 2015| Pages o105-o106

doi:10.1107/S2056989015000286

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

Crystal structure of (E)-3-{[2-(2,4-di­chloro­benzyl­­idene)hydrazin-1-yl]carbon­yl}pyridinium chloride trihydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-3-{[2-(2,4-dichlorobenzylidene)hydrazin-1-yl]carbonyl}pyridinium chloride trihydrate