(Pyridin-4-yl)methyl N′-(3-phenyl­allyl­idene)hydrazinecarbodithio­ate

Low, M.L.; Ravoof, T.B.S.A.; Tahir, M.I.M.; Crouse, K.A.; Tiekink, E.R.T.

doi:10.1107/S1600536812051537

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o167-o168

doi:10.1107/S1600536812051537

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(Pyridin-4-yl)methyl N′-(3-phenylallylidene)hydrazinecarbodithioate

May Lee Low,^a Thahira Begum S. A. Ravoof,^a Mohamed Ibrahim Mohamed Tahir,^a Karen A. Crouse ^a ‡ and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 20 December 2012; accepted 20 December 2012; online 4 January 2013)

In the title compound, C₁₆H₁₅N₃S₂, the central C₂N₂S₂ residue is planar (r.m.s. deviation = 0.045 Å) and the pyridyl and benzene rings are inclined and approximately coplanar to this plane, respectively [dihedral angles = 72.85 (9) and 10.73 (9)°], so that, overall, the molecule adopts an L-shape. The conformation about each of the N=C [1.290 (3) Å] and C=C [1.340 (3) Å] bonds is E. Supramolecular chains along [1-10] are stabilized by N—H⋯N(pyridine) hydrogen bonding and these are connected into a double layer that stacks along the c-axis direction by C—H⋯π(pyridine) interactions.

Related literature

For background to related Schiff bases of S-substituted dithiocarbazates with cinnamaldehyde, see: Tarafder et al. (2008 , 2010 ). For the corresponding metal complexes, see: Reza et al. (2012 ); Liu et al. (2009 ). For the biological activity of similar sulfur–nitrogen-containing Schiff base derivatives, see: Maia et al. (2010 ); Pavan et al. (2010 ); Zhu et al. (2009 ). For the synthesis, see: Crouse et al. (2004 ); Khoo (2008 ); Tarafder et al. (2008, 2010).

Experimental

Crystal data

C₁₆H₁₅N₃S₂
M_r = 313.43
Triclinic, $[P \overline 1]$
a = 5.3784 (5) Å
b = 10.1570 (9) Å
c = 14.5488 (17) Å
α = 77.315 (9)°
β = 84.735 (9)°
γ = 78.193 (8)°
V = 758.06 (13) Å³
Z = 2
Cu Kα radiation
μ = 3.14 mm⁻¹
T = 100 K
0.13 × 0.06 × 0.01 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.83, T_max = 0.97
15664 measured reflections
2918 independent reflections
2469 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.115
S = 1.05
2918 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N3,C12–C15 pyridyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N3ⁱ	0.88 (2)	2.02 (2)	2.897 (3)	172 (2)
C8—H8⋯Cg1ⁱⁱ	0.95	2.92	3.701 (3)	141
Symmetry codes: (i) x+1, y-1, z; (ii) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812051537/qm2090sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051537/qm2090Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051537/qm2090Isup3.cml

checkCIF report

Comment top

Schiff bases of S-substituted dithiocarbazates with cinnamaldehyde attract interest in terms of both coordination chemistry (Reza et al., 2012; Liu et al., 2009) and for their biological activities (Maia et al., 2010; Pavan et al., 2010; Zhu et al., 2009. In pursuing our continuing interest in the coordination chemistry of dithiocarbazate derivatives and their biological importance (Tarafder et al., 2010; Tarafder et al., 2008), the title compound, (I), the product of condensation between S-4-picolyl dithiocarbazate and cinnamaldehyde, was investigated.

In (I), Fig. 1, the central C₂N₂S₂ residue is planar (r.m.s. deviation = 0.045 Å) with maximum deviations of 0.040 (2) Å for each of N1 and C11, and -0.048 (1) Å for the S1 atom. The pyridyl ring is inclined to this plane, forming a dihedral angle of 72.85 (9) °, whereas the benzene ring is almost co-planar [dihedral angle = 10.73 (9)°]. The maximum twist from co-planarity along the C₅N₂ chain is seen in the C1—N1—N2—C2 torsion angle of -176.15 (19) Å. The amine-N1—H atom is syn to the thione-S2 atom. The conformation about each of the N2═C2 [1.290 (3) Å] and C3═C4 [1.340 (3) Å] bonds is E. Globally, the molecule adopts an L-shape as the pyridyl residue is anti to the thione-S2 atom. A very similar conformation was found in the benzyl ester (Tarafder et al., 2008).

The pyridyl ring proves pivotal in the crystal packing by forming a hydrogen bond with the amine-N1—H atom and acting as an acceptor in a C—H···π(pyridyl) contact, Table 1. The hydrogen bonding leads to the formation of supramolecular chains along [1 1 0] and these are connected into a double layer in the ab plane via the C—H···π(pyridyl) contacts, Fig. 2.

Related literature top

For background to related Schiff bases of S-substituted dithiocarbazates with cinnamaldehyde, see: Tarafder et al. (2008, 2010). For the corresponding metal complexes, see: Reza et al. (2012); Liu et al. (2009). For the biological activity of similar sulfur–nitrogen-containing Schiff base derivatives, see: Maia et al. (2010); Pavan et al. (2010); Zhu et al. (2009). For the synthesis, see: Crouse et al. (2004); Khoo (2008); Tarafder et al. (2008, 2010).

Experimental top

The previously reported method for preparation substituted dithiocarbazate (Crouse et al., 2004) was modified by reaction with 4-picolylchloride hydrochloride (Khoo, 2008).

Potassium hydroxide (11.4 g, 0.2 mol) was dissolved completely in 90% ethanol (70 ml) and the mixture was cooled in ice. To the cold solution, hydrazine hydrate (9.7 ml, 0.2 mol) was added slowly with stirring. Carbon disulfide (12.0 ml, 0.2 mol) was then added drop-wise with vigorous stirring for about 1 h. The temperature of the reaction mixture was kept below 268 K during addition. During this time two layers formed. The resulting yellow oil (lower layer) was separated and dissolved in 40% ethanol (60 ml). 4-Picolylchloride hydrochloride (32.8 g, 0.2 mol) was completely dissolved in 100 ml of 80% ethanol and added slowly to the above solution with vigorous mechanical stirring. The resulting white product (S4PDTC) was separated by filtration, washed with water and dried. The crude product was recrystallized from absolute ethanol.

Previously reported methods for preparation of Schiff bases (Tarafder et al., 2010; Tarafder et al., 2008) were used to prepare S4PDTC derivatives with cinnamaldehyde. An equimolar amount of cinnamaldehyde (1.26 ml) was added to the solution of S4PDTC (1.99 g, 0.01 mol) dissolved in hot absolute ethanol (100 ml). The mixture was heated while being stirred to reduce it to half the original volume and then cooled. The orange compound was filtered, washed with absolute ethanol then dried over silica gel. Single crystals were obtained after recrystallization from a mixture of DMF/chloroform. (yield 72%, M.pt: 481–482 K).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the crystal packing in projection down the a axis, highlighting the stacking of supramolecular layers along the c axis. The N—H···N and C—H···π interactions are shown as blue and purple dashed lines, respectively.

(Pyridin-4-yl)methyl N'-(3-phenylallylidene)hydrazinecarbodithioate top

Crystal data top

C₁₆H₁₅N₃S₂	Z = 2
M_r = 313.43	F(000) = 328
Triclinic, P1	D_x = 1.373 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.3784 (5) Å	Cell parameters from 5833 reflections
b = 10.1570 (9) Å	θ = 3–72°
c = 14.5488 (17) Å	µ = 3.14 mm⁻¹
α = 77.315 (9)°	T = 100 K
β = 84.735 (9)°	Thin-plate, orange
γ = 78.193 (8)°	0.13 × 0.06 × 0.01 mm
V = 758.06 (13) Å³

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	2918 independent reflections
Radiation source: fine-focus sealed tube	2469 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 16.1952 pixels mm^-1	θ_max = 72.3°, θ_min = 3.1°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
T_min = 0.83, T_max = 0.97	l = −17→15
15664 measured 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0669P)² + 0.3038P] where P = (F_o² + 2F_c²)/3
2918 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.42 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₆H₁₅N₃S₂	γ = 78.193 (8)°
M_r = 313.43	V = 758.06 (13) Å³
Triclinic, P1	Z = 2
a = 5.3784 (5) Å	Cu Kα radiation
b = 10.1570 (9) Å	µ = 3.14 mm⁻¹
c = 14.5488 (17) Å	T = 100 K
α = 77.315 (9)°	0.13 × 0.06 × 0.01 mm
β = 84.735 (9)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	2918 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2469 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.97	R_int = 0.045
15664 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.42 e Å⁻³
2918 reflections	Δρ_min = −0.29 e Å⁻³
193 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.36876 (9)	0.53086 (5)	0.18295 (4)	0.02532 (16)
S2	0.33320 (10)	0.32045 (5)	0.06781 (4)	0.02701 (17)
N1	0.6775 (3)	0.29601 (17)	0.19095 (13)	0.0256 (4)
H1n	0.749 (4)	0.2148 (14)	0.1794 (18)	0.031*
N2	0.7786 (3)	0.34184 (17)	0.25917 (13)	0.0262 (4)
N3	−0.1177 (4)	1.01818 (18)	0.16683 (15)	0.0338 (5)
C1	0.4717 (4)	0.3730 (2)	0.14713 (15)	0.0233 (4)
C2	0.9846 (4)	0.2638 (2)	0.29282 (16)	0.0266 (5)
H2	1.0579	0.1846	0.2682	0.032*
C3	1.1038 (4)	0.2962 (2)	0.36748 (16)	0.0284 (5)
H3	1.0295	0.3764	0.3909	0.034*
C4	1.3162 (4)	0.2171 (2)	0.40512 (16)	0.0279 (5)
H4	1.3893	0.1405	0.3776	0.033*
C5	1.4484 (4)	0.2350 (2)	0.48372 (16)	0.0284 (5)
C6	1.3649 (5)	0.3430 (2)	0.53137 (18)	0.0370 (6)
H6	1.2139	0.4074	0.5133	0.044*
C7	1.4982 (5)	0.3574 (3)	0.60420 (19)	0.0393 (6)
H7	1.4401	0.4323	0.6349	0.047*
C8	1.7160 (5)	0.2633 (3)	0.63253 (18)	0.0368 (6)
H8	1.8074	0.2733	0.6826	0.044*
C9	1.8000 (4)	0.1543 (3)	0.58746 (18)	0.0359 (5)
H9	1.9484	0.0889	0.6072	0.043*
C10	1.6683 (4)	0.1405 (2)	0.51347 (17)	0.0312 (5)
H10	1.7283	0.0659	0.4827	0.037*
C11	0.1118 (4)	0.6125 (2)	0.10459 (17)	0.0269 (5)
H11A	0.1725	0.6164	0.0379	0.032*
H11B	−0.0298	0.5612	0.1181	0.032*
C12	0.0263 (4)	0.7559 (2)	0.12385 (16)	0.0262 (5)
C13	−0.1950 (4)	0.7908 (2)	0.17696 (19)	0.0357 (6)
H13	−0.3022	0.7258	0.1998	0.043*
C14	−0.2588 (4)	0.9219 (2)	0.1965 (2)	0.0390 (6)
H14	−0.4112	0.9441	0.2330	0.047*
C15	0.0961 (5)	0.9839 (2)	0.11574 (18)	0.0345 (5)
H15	0.1999	1.0508	0.0940	0.041*
C16	0.1742 (4)	0.8555 (2)	0.09283 (17)	0.0314 (5)
H16	0.3277	0.8361	0.0562	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0270 (3)	0.0170 (3)	0.0333 (3)	0.00106 (19)	−0.0078 (2)	−0.0104 (2)
S2	0.0278 (3)	0.0215 (3)	0.0342 (3)	−0.0011 (2)	−0.0060 (2)	−0.0124 (2)
N1	0.0275 (9)	0.0184 (8)	0.0315 (10)	0.0004 (7)	−0.0035 (8)	−0.0100 (7)
N2	0.0260 (9)	0.0226 (9)	0.0312 (10)	−0.0014 (7)	−0.0049 (7)	−0.0095 (7)
N3	0.0309 (10)	0.0233 (9)	0.0484 (13)	0.0048 (7)	−0.0124 (9)	−0.0149 (9)
C1	0.0249 (10)	0.0176 (9)	0.0272 (11)	−0.0021 (8)	0.0002 (8)	−0.0062 (8)
C2	0.0251 (10)	0.0224 (10)	0.0323 (12)	−0.0021 (8)	−0.0013 (9)	−0.0078 (9)
C3	0.0292 (11)	0.0234 (10)	0.0334 (12)	−0.0025 (8)	−0.0023 (9)	−0.0096 (9)
C4	0.0300 (11)	0.0238 (10)	0.0299 (12)	−0.0020 (8)	0.0003 (9)	−0.0089 (9)
C5	0.0271 (11)	0.0262 (11)	0.0313 (12)	−0.0045 (8)	−0.0021 (9)	−0.0051 (9)
C6	0.0370 (13)	0.0302 (12)	0.0429 (15)	0.0047 (9)	−0.0111 (11)	−0.0122 (10)
C7	0.0419 (14)	0.0341 (13)	0.0436 (15)	0.0009 (10)	−0.0083 (11)	−0.0166 (11)
C8	0.0345 (12)	0.0433 (14)	0.0341 (13)	−0.0045 (10)	−0.0093 (10)	−0.0111 (11)
C9	0.0281 (11)	0.0395 (13)	0.0387 (14)	0.0020 (9)	−0.0057 (10)	−0.0111 (11)
C10	0.0291 (11)	0.0303 (11)	0.0339 (13)	−0.0007 (9)	−0.0007 (9)	−0.0108 (9)
C11	0.0268 (10)	0.0201 (10)	0.0344 (12)	0.0004 (8)	−0.0097 (9)	−0.0077 (9)
C12	0.0270 (10)	0.0198 (10)	0.0320 (12)	0.0022 (8)	−0.0113 (9)	−0.0081 (8)
C13	0.0260 (11)	0.0314 (12)	0.0542 (16)	−0.0051 (9)	−0.0020 (10)	−0.0185 (11)
C14	0.0257 (11)	0.0359 (13)	0.0584 (17)	0.0018 (9)	−0.0017 (11)	−0.0235 (12)
C15	0.0389 (13)	0.0204 (10)	0.0439 (14)	−0.0034 (9)	−0.0068 (11)	−0.0060 (9)
C16	0.0328 (11)	0.0230 (10)	0.0363 (13)	0.0005 (9)	−0.0022 (10)	−0.0071 (9)

Geometric parameters (Å, º) top

S1—C1	1.760 (2)	C7—C8	1.383 (3)
S1—C11	1.817 (2)	C7—H7	0.9500
S2—C1	1.662 (2)	C8—C9	1.385 (4)
N1—C1	1.342 (3)	C8—H8	0.9500
N1—N2	1.379 (3)	C9—C10	1.389 (3)
N1—H1n	0.880 (10)	C9—H9	0.9500
N2—C2	1.290 (3)	C10—H10	0.9500
N3—C14	1.332 (3)	C11—C12	1.514 (3)
N3—C15	1.337 (3)	C11—H11A	0.9900
C2—C3	1.439 (3)	C11—H11B	0.9900
C2—H2	0.9500	C12—C13	1.385 (3)
C3—C4	1.340 (3)	C12—C16	1.386 (3)
C3—H3	0.9500	C13—C14	1.391 (3)
C4—C5	1.463 (3)	C13—H13	0.9500
C4—H4	0.9500	C14—H14	0.9500
C5—C10	1.398 (3)	C15—C16	1.389 (3)
C5—C6	1.400 (3)	C15—H15	0.9500
C6—C7	1.382 (3)	C16—H16	0.9500
C6—H6	0.9500

C1—S1—C11	101.51 (10)	C9—C8—H8	120.2
C1—N1—N2	119.67 (17)	C8—C9—C10	120.2 (2)
C1—N1—H1n	122.4 (17)	C8—C9—H9	119.9
N2—N1—H1n	117.9 (17)	C10—C9—H9	119.9
C2—N2—N1	114.56 (18)	C9—C10—C5	120.9 (2)
C14—N3—C15	116.84 (19)	C9—C10—H10	119.6
N1—C1—S2	121.98 (16)	C5—C10—H10	119.6
N1—C1—S1	113.13 (16)	C12—C11—S1	105.44 (14)
S2—C1—S1	124.88 (12)	C12—C11—H11A	110.7
N2—C2—C3	120.4 (2)	S1—C11—H11A	110.7
N2—C2—H2	119.8	C12—C11—H11B	110.7
C3—C2—H2	119.8	S1—C11—H11B	110.7
C4—C3—C2	122.2 (2)	H11A—C11—H11B	108.8
C4—C3—H3	118.9	C13—C12—C16	117.4 (2)
C2—C3—H3	118.9	C13—C12—C11	121.6 (2)
C3—C4—C5	127.5 (2)	C16—C12—C11	121.0 (2)
C3—C4—H4	116.3	C12—C13—C14	119.3 (2)
C5—C4—H4	116.3	C12—C13—H13	120.3
C10—C5—C6	117.9 (2)	C14—C13—H13	120.3
C10—C5—C4	119.1 (2)	N3—C14—C13	123.6 (2)
C6—C5—C4	123.0 (2)	N3—C14—H14	118.2
C7—C6—C5	121.1 (2)	C13—C14—H14	118.2
C7—C6—H6	119.4	N3—C15—C16	123.4 (2)
C5—C6—H6	119.4	N3—C15—H15	118.3
C6—C7—C8	120.2 (2)	C16—C15—H15	118.3
C6—C7—H7	119.9	C12—C16—C15	119.4 (2)
C8—C7—H7	119.9	C12—C16—H16	120.3
C7—C8—C9	119.7 (2)	C15—C16—H16	120.3
C7—C8—H8	120.2

C1—N1—N2—C2	−176.15 (19)	C8—C9—C10—C5	−0.5 (4)
N2—N1—C1—S2	−177.22 (15)	C6—C5—C10—C9	−0.5 (3)
N2—N1—C1—S1	2.5 (2)	C4—C5—C10—C9	179.6 (2)
C11—S1—C1—N1	175.41 (16)	C1—S1—C11—C12	−174.77 (15)
C11—S1—C1—S2	−4.84 (16)	S1—C11—C12—C13	−103.5 (2)
N1—N2—C2—C3	−177.19 (18)	S1—C11—C12—C16	73.2 (2)
N2—C2—C3—C4	179.2 (2)	C16—C12—C13—C14	0.1 (4)
C2—C3—C4—C5	−176.9 (2)	C11—C12—C13—C14	176.9 (2)
C3—C4—C5—C10	179.6 (2)	C15—N3—C14—C13	−0.1 (4)
C3—C4—C5—C6	−0.2 (4)	C12—C13—C14—N3	0.0 (4)
C10—C5—C6—C7	1.3 (4)	C14—N3—C15—C16	0.2 (4)
C4—C5—C6—C7	−178.8 (2)	C13—C12—C16—C15	0.0 (3)
C5—C6—C7—C8	−1.1 (4)	C11—C12—C16—C15	−176.9 (2)
C6—C7—C8—C9	0.1 (4)	N3—C15—C16—C12	−0.1 (4)
C7—C8—C9—C10	0.8 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N3,C12–C15 pyridyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N3ⁱ	0.88 (2)	2.02 (2)	2.897 (3)	172 (2)
C8—H8···Cg1ⁱⁱ	0.95	2.92	3.701 (3)	141

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₃S₂
M_r	313.43
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.3784 (5), 10.1570 (9), 14.5488 (17)
α, β, γ (°)	77.315 (9), 84.735 (9), 78.193 (8)
V (Å³)	758.06 (13)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	3.14
Crystal size (mm)	0.13 × 0.06 × 0.01

Data collection
Diffractometer	Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.83, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	15664, 2918, 2469
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.115, 1.05
No. of reflections	2918
No. of parameters	193
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.29

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N3,C12–C15 pyridyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N3ⁱ	0.881 (16)	2.021 (15)	2.897 (3)	172 (2)
C8—H8···Cg1ⁱⁱ	0.95	2.92	3.701 (3)	141

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

Footnotes

‡Additional correspondence author, e-mail: crouse@pc.jaring.my.

Acknowledgements

Support for this project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS 9174000) and the Malaysian Ministry of Science Technology and Innovation (MOSTI 09–02-04–9752EA001) and the Malaysian Fundamental Research Grant Scheme (FRGS 01–13-11–986FR). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

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Volume 69| Part 2| February 2013| Pages o167-o168

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