(E)-N′-[(E)-2-Methyl­pent-2-enyl­idene]isonicotinohydrazide

Naveenkumar, H.S.; Sadikun, A.; Ibrahim, P.; Loh, W.-S.; Fun, H.-K.

doi:10.1107/S1600536810019434

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages o1489-o1490

https://doi.org/10.1107/S1600536810019434

Open

access

(E)-N′-[(E)-2-Methylpent-2-enylidene]isonicotinohydrazide

H. S. Naveenkumar,^a Amirin Sadikun,^a ‡ Pazilah Ibrahim,^a Wan-Sin Loh ^b § and Hoong-Kun Fun ^b ^*¶

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 20 May 2010; accepted 24 May 2010; online 29 May 2010)

The asymmetric unit of the title Schiff base compound, C₁₂H₁₅N₃O, contains two crystallographically independent molecules, with both existing in an E configuration with respect to the C=N double bonds. In the crystal structure, intermolecular N—H⋯N and C—H⋯O hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For the applications of isoniazid derivatives, see: Janin (2007 ); Maccari et al. (2005 ); Slayden & Barry (2000 ). For the biological activity of Schiff bases, see: Kahwa et al. (1986 ). For related structures, see: Naveenkumar et al. (2009 ); Naveenkumar, Sadikun, Ibrahim, Quah & Fun (2010 ); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2010 ); Shi (2005 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ). For the synthesis, see: Lourenco et al. (2008 ).

Experimental

Crystal data

C₁₂H₁₅N₃O
M_r = 217.27
Monoclinic, C c
a = 19.809 (4) Å
b = 8.3459 (15) Å
c = 16.021 (3) Å
β = 119.825 (3)°
V = 2297.7 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.54 × 0.20 × 0.10 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.957, T_max = 0.992
12644 measured reflections
3396 independent reflections
2883 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.225
S = 1.03
3396 reflections
301 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.15 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2B—H1NB⋯N1Aⁱ	0.95 (6)	2.08 (6)	2.973 (5)	156 (5)
N2A—H1NA⋯N1Bⁱⁱ	0.83 (6)	2.26 (6)	3.005 (5)	148 (5)
C7B—H7BA⋯O1Aⁱⁱⁱ	0.93	2.51	3.171 (5)	129
C12A—H12B⋯O1B	0.96	2.48	3.433 (5)	173
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+2, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810019434/is2553sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810019434/is2553Isup2.hkl

checkCIF report

Comment top

In the search of new compounds, isoniazid derivatives have been found to possess potential tuberculostatic activity (Janin, 2007; Maccari et al., 2005; Slayden et al., 2000). Schiff bases have attracted much attention because of their biological activity (Kahwa et al., 1986). As a part of a current work of synthesis of (E)-N'-substituted isonicotinohydrazide derivatives, in this paper we present the crystal structure of the title compound.

The title Schiff base compound (Fig. 1), consists of two crystallographically independent molecules (molecule A & B). In the molecules, both pyridine rings (C1A/C2A/N1A/C3A–C5A & C1B/C2B/N1B/C3B–C5B) are approximately planar with maximum deviations of 0.006 (5) Å at atom C4A and 0.007 (6) Å at atom C3B. The molecules exist in an E configuration with respect to the C7A═N3A and C7B═N3B double bonds. Bond lengths (Allen et al., 1987) and the angles of the title compound are within the normal range and are closely related to comparable structures (Naveenkumar et al., 2009; Naveenkumar, Sadikun, Ibrahim, Quah & Fun, 2010; Naveenkumar, Sadikun, Ibrahim, Yeap & Fun, 2010; Shi, 2005).

In the crystal packing (Fig. 2), intermolecular N2B—H1NB···N1A, N2A—H1NA···N1B, C7B—H7BA···O1A and C12A—H12B···O1B hydrogen bonds (Table 1) link the molecules into a three-dimensional network.

Related literature top

For the applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000). For the biological activity of Schiff bases, see: Kahwa et al. (1986). For related structures, see: Naveenkumar et al. (2009); Naveenkumar, Sadikun, Ibrahim, Quah & Fun (2010); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2010); Shi (2005). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For the synthesis, see: Lourenco et al. (2008).

Experimental top

The isoniazid derivative was prepared following the procedure by Lourenco et al. (2008). The titled compound was prepared by reaction between the 2-methyl-2-pentenal (1.0 eq) with isoniazid (1.0 eq) in ethanol/water. After stirring for 1-3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue, purified by washing with cold ethanol and ethyl ether, afforded the pure derivative. The colourless single crystal suitable for X-ray analysis was obtained by recrystalization with methanol.

Structure description top

For the applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000). For the biological activity of Schiff bases, see: Kahwa et al. (1986). For related structures, see: Naveenkumar et al. (2009); Naveenkumar, Sadikun, Ibrahim, Quah & Fun (2010); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2010); Shi (2005). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For the synthesis, see: Lourenco et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Intermolecular interactions are shown as dashed lines. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

(E)-N'-[(E)-2-Methylpent-2-enylidene]isonicotinohydrazide top

Crystal data top

C₁₂H₁₅N₃O	F(000) = 928
M_r = 217.27	D_x = 1.256 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3734 reflections
a = 19.809 (4) Å	θ = 2.7–30.1°
b = 8.3459 (15) Å	µ = 0.08 mm⁻¹
c = 16.021 (3) Å	T = 100 K
β = 119.825 (3)°	Plate, colourless
V = 2297.7 (7) Å³	0.54 × 0.20 × 0.10 mm
Z = 8

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3396 independent reflections
Radiation source: fine-focus sealed tube	2883 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
φ and ω scans	θ_max = 30.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −28→27
T_min = 0.957, T_max = 0.992	k = −11→11
12644 measured reflections	l = −22→22

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.225	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.158P)² + 2.1081P] where P = (F_o² + 2F_c²)/3
3396 reflections	(Δ/σ)_max = 0.001
301 parameters	Δρ_max = 1.15 e Å⁻³
2 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₂H₁₅N₃O	V = 2297.7 (7) Å³
M_r = 217.27	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 19.809 (4) Å	µ = 0.08 mm⁻¹
b = 8.3459 (15) Å	T = 100 K
c = 16.021 (3) Å	0.54 × 0.20 × 0.10 mm
β = 119.825 (3)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3396 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2883 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.992	R_int = 0.044
12644 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	2 restraints
wR(F²) = 0.225	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 1.15 e Å⁻³
3396 reflections	Δρ_min = −0.47 e Å⁻³
301 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1A	0.45226 (16)	0.4174 (4)	0.2514 (2)	0.0279 (6)
N1A	0.50282 (19)	0.5795 (5)	−0.0143 (2)	0.0270 (7)
N2A	0.33160 (18)	0.4903 (4)	0.1323 (2)	0.0222 (6)
N3A	0.29513 (18)	0.4476 (4)	0.1835 (2)	0.0222 (6)
C1A	0.3923 (2)	0.5171 (5)	0.0042 (2)	0.0228 (7)
H1AA	0.3391	0.4982	−0.0247	0.027*
C2A	0.4267 (2)	0.5523 (5)	−0.0517 (3)	0.0245 (7)
H2AA	0.3950	0.5570	−0.1182	0.029*
C3A	0.5470 (2)	0.5727 (6)	0.0815 (3)	0.0332 (9)
H3AA	0.6000	0.5926	0.1087	0.040*
C4A	0.5184 (2)	0.5376 (6)	0.1427 (3)	0.0307 (8)
H4AA	0.5516	0.5322	0.2089	0.037*
C5A	0.4391 (2)	0.5108 (5)	0.1032 (3)	0.0233 (7)
C6A	0.4089 (2)	0.4684 (5)	0.1703 (2)	0.0219 (7)
C7A	0.2215 (2)	0.4758 (4)	0.1376 (3)	0.0224 (6)
H7AA	0.1994	0.5197	0.0762	0.027*
C8A	0.1715 (2)	0.4418 (5)	0.1777 (3)	0.0256 (7)
C9A	0.0963 (3)	0.4814 (6)	0.1240 (3)	0.0356 (9)
H9AA	0.0812	0.5247	0.0638	0.043*
C10A	0.0337 (3)	0.4641 (7)	0.1499 (4)	0.0429 (11)
H10A	0.0568	0.4299	0.2164	0.052*
H10B	−0.0026	0.3818	0.1099	0.052*
C11A	−0.0096 (3)	0.6178 (7)	0.1369 (4)	0.0448 (12)
H11A	−0.0508	0.6005	0.1510	0.067*
H11B	−0.0311	0.6539	0.0717	0.067*
H11C	0.0254	0.6975	0.1798	0.067*
C12A	0.2060 (2)	0.3646 (6)	0.2752 (3)	0.0301 (8)
H12A	0.1734	0.2774	0.2727	0.045*
H12B	0.2096	0.4422	0.3214	0.045*
H12C	0.2570	0.3248	0.2936	0.045*
O1B	0.20324 (15)	0.6331 (3)	0.4358 (2)	0.0268 (6)
N1B	0.2523 (2)	1.2198 (4)	0.5118 (3)	0.0330 (8)
N2B	0.08523 (17)	0.7236 (4)	0.4095 (2)	0.0236 (6)
N3B	0.04966 (18)	0.5750 (4)	0.3851 (2)	0.0241 (6)
C1B	0.14199 (19)	1.0456 (5)	0.4260 (2)	0.0219 (7)
H1BA	0.0886	1.0349	0.3852	0.026*
C2B	0.1756 (2)	1.1958 (5)	0.4529 (3)	0.0256 (7)
H2BA	0.1434	1.2851	0.4291	0.031*
C3B	0.2969 (3)	1.0896 (6)	0.5452 (4)	0.0464 (13)
H3BA	0.3499	1.1039	0.5869	0.056*
C4B	0.2692 (2)	0.9350 (5)	0.5217 (4)	0.0392 (11)
H4BA	0.3030	0.8483	0.5459	0.047*
C5B	0.1895 (2)	0.9105 (4)	0.4610 (3)	0.0241 (7)
C6B	0.1606 (2)	0.7417 (4)	0.4338 (2)	0.0230 (7)
C7B	−0.0233 (2)	0.5835 (5)	0.3572 (3)	0.0286 (8)
H7BA	−0.0463	0.6834	0.3502	0.034*
C8B	−0.0706 (2)	0.4398 (5)	0.3366 (4)	0.0354 (10)
C9B	−0.1419 (3)	0.4525 (7)	0.3267 (5)	0.0529 (15)
H9BA	−0.1580	0.5559	0.3297	0.063*
C10B	−0.1989 (3)	0.3214 (7)	0.3113 (5)	0.0497 (13)
H10C	−0.1876	0.2290	0.2836	0.060*
H10D	−0.1926	0.2896	0.3730	0.060*
C11B	−0.2777 (4)	0.3700 (8)	0.2492 (8)	0.072 (2)
H11D	−0.3123	0.2879	0.2476	0.108*
H11E	−0.2861	0.3870	0.1855	0.108*
H11F	−0.2876	0.4677	0.2729	0.108*
C12B	−0.0352 (3)	0.2825 (5)	0.3361 (4)	0.0387 (10)
H12D	−0.0744	0.2008	0.3132	0.058*
H12E	0.0050	0.2568	0.4002	0.058*
H12F	−0.0132	0.2886	0.2946	0.058*
H1NB	0.059 (3)	0.808 (7)	0.421 (4)	0.023 (11)*
H1NA	0.306 (3)	0.543 (7)	0.082 (4)	0.028 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0188 (12)	0.0390 (16)	0.0207 (12)	0.0013 (11)	0.0059 (10)	0.0045 (11)
N1A	0.0189 (14)	0.0374 (18)	0.0235 (15)	−0.0008 (12)	0.0098 (12)	0.0006 (13)
N2A	0.0157 (13)	0.0295 (15)	0.0201 (14)	0.0012 (11)	0.0079 (11)	0.0049 (12)
N3A	0.0198 (14)	0.0243 (14)	0.0219 (13)	−0.0011 (11)	0.0099 (11)	0.0020 (11)
C1A	0.0157 (14)	0.0303 (17)	0.0187 (15)	−0.0021 (12)	0.0056 (12)	−0.0013 (13)
C2A	0.0175 (15)	0.0339 (19)	0.0173 (14)	0.0015 (13)	0.0051 (12)	0.0014 (13)
C3A	0.0150 (15)	0.055 (3)	0.0224 (17)	−0.0095 (16)	0.0041 (13)	0.0000 (17)
C4A	0.0162 (16)	0.048 (2)	0.0202 (16)	−0.0066 (15)	0.0030 (13)	0.0004 (15)
C5A	0.0122 (14)	0.0301 (17)	0.0211 (15)	−0.0009 (12)	0.0034 (12)	0.0021 (13)
C6A	0.0161 (14)	0.0251 (16)	0.0195 (15)	−0.0022 (12)	0.0051 (12)	−0.0028 (12)
C7A	0.0184 (15)	0.0255 (16)	0.0196 (14)	0.0002 (12)	0.0067 (12)	0.0020 (13)
C8A	0.0186 (16)	0.0363 (19)	0.0204 (16)	0.0034 (14)	0.0087 (13)	0.0004 (14)
C9A	0.0235 (19)	0.052 (3)	0.0292 (19)	0.0060 (18)	0.0117 (16)	0.0065 (19)
C10A	0.030 (2)	0.050 (3)	0.052 (3)	0.006 (2)	0.024 (2)	0.008 (2)
C11A	0.038 (3)	0.050 (3)	0.052 (3)	0.009 (2)	0.026 (2)	0.005 (2)
C12A	0.0236 (17)	0.040 (2)	0.0255 (17)	0.0012 (15)	0.0113 (14)	0.0032 (16)
O1B	0.0165 (11)	0.0251 (12)	0.0306 (13)	0.0023 (9)	0.0056 (10)	−0.0032 (11)
N1B	0.0257 (16)	0.0244 (15)	0.0346 (17)	−0.0034 (13)	0.0042 (14)	−0.0038 (14)
N2B	0.0130 (12)	0.0264 (15)	0.0249 (14)	−0.0001 (11)	0.0046 (11)	−0.0037 (12)
N3B	0.0202 (14)	0.0238 (14)	0.0230 (14)	−0.0024 (11)	0.0066 (12)	−0.0003 (11)
C1B	0.0153 (14)	0.0267 (17)	0.0189 (14)	0.0028 (12)	0.0049 (12)	0.0007 (12)
C2B	0.0231 (16)	0.0265 (17)	0.0236 (15)	0.0000 (13)	0.0088 (13)	−0.0017 (13)
C3B	0.0202 (18)	0.031 (2)	0.055 (3)	−0.0013 (16)	−0.0055 (18)	−0.008 (2)
C4B	0.0148 (16)	0.0258 (18)	0.050 (3)	0.0010 (13)	−0.0046 (16)	−0.0063 (17)
C5B	0.0164 (14)	0.0235 (16)	0.0236 (16)	0.0006 (12)	0.0034 (13)	−0.0033 (13)
C6B	0.0181 (15)	0.0240 (16)	0.0200 (14)	−0.0001 (12)	0.0043 (12)	−0.0018 (12)
C7B	0.0191 (15)	0.0243 (17)	0.0342 (19)	−0.0018 (13)	0.0071 (14)	−0.0075 (15)
C8B	0.0235 (18)	0.0281 (19)	0.050 (3)	−0.0089 (15)	0.0144 (18)	−0.0160 (18)
C9B	0.032 (2)	0.040 (3)	0.081 (4)	−0.010 (2)	0.023 (3)	−0.021 (3)
C10B	0.041 (3)	0.041 (3)	0.064 (3)	−0.006 (2)	0.023 (3)	−0.006 (2)
C11B	0.055 (4)	0.044 (3)	0.137 (8)	−0.010 (3)	0.063 (5)	−0.020 (4)
C12B	0.036 (2)	0.0262 (19)	0.063 (3)	−0.0065 (16)	0.032 (2)	−0.0093 (19)

Geometric parameters (Å, º) top

O1A—C6A	1.223 (5)	O1B—C6B	1.228 (5)
N1A—C2A	1.337 (5)	N1B—C3B	1.333 (6)
N1A—C3A	1.338 (5)	N1B—C2B	1.346 (5)
N2A—C6A	1.350 (4)	N2B—C6B	1.350 (4)
N2A—N3A	1.382 (4)	N2B—N3B	1.383 (4)
N2A—H1NA	0.83 (6)	N2B—H1NB	0.94 (6)
N3A—C7A	1.287 (5)	N3B—C7B	1.284 (5)
C1A—C5A	1.384 (5)	C1B—C2B	1.384 (5)
C1A—C2A	1.399 (5)	C1B—C5B	1.395 (5)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.385 (6)	C3B—C4B	1.379 (6)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.389 (5)	C4B—C5B	1.397 (5)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.510 (5)	C5B—C6B	1.502 (5)
C7A—C8A	1.451 (5)	C7B—C8B	1.456 (6)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.340 (5)	C8B—C9B	1.344 (7)
C8A—C12A	1.503 (5)	C8B—C12B	1.490 (6)
C9A—C10A	1.496 (6)	C9B—C10B	1.502 (8)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.499 (8)	C10B—C11B	1.431 (10)
C10A—H10A	0.9700	C10B—H10C	0.9700
C10A—H10B	0.9700	C10B—H10D	0.9700
C11A—H11A	0.9600	C11B—H11D	0.9600
C11A—H11B	0.9600	C11B—H11E	0.9600
C11A—H11C	0.9600	C11B—H11F	0.9600
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600

C2A—N1A—C3A	117.0 (3)	C3B—N1B—C2B	116.8 (4)
C6A—N2A—N3A	120.5 (3)	C6B—N2B—N3B	121.1 (3)
C6A—N2A—H1NA	121 (4)	C6B—N2B—H1NB	119 (3)
N3A—N2A—H1NA	117 (4)	N3B—N2B—H1NB	119 (3)
C7A—N3A—N2A	113.0 (3)	C7B—N3B—N2B	112.1 (3)
C5A—C1A—C2A	118.6 (3)	C2B—C1B—C5B	118.9 (3)
C5A—C1A—H1AA	120.7	C2B—C1B—H1BA	120.6
C2A—C1A—H1AA	120.7	C5B—C1B—H1BA	120.6
N1A—C2A—C1A	123.3 (3)	N1B—C2B—C1B	123.6 (4)
N1A—C2A—H2AA	118.3	N1B—C2B—H2BA	118.2
C1A—C2A—H2AA	118.3	C1B—C2B—H2BA	118.2
N1A—C3A—C4A	123.9 (4)	N1B—C3B—C4B	124.0 (4)
N1A—C3A—H3AA	118.1	N1B—C3B—H3BA	118.0
C4A—C3A—H3AA	118.1	C4B—C3B—H3BA	118.0
C3A—C4A—C5A	118.6 (4)	C3B—C4B—C5B	119.0 (4)
C3A—C4A—H4AA	120.7	C3B—C4B—H4BA	120.5
C5A—C4A—H4AA	120.7	C5B—C4B—H4BA	120.5
C1A—C5A—C4A	118.5 (3)	C1B—C5B—C4B	117.7 (3)
C1A—C5A—C6A	123.3 (3)	C1B—C5B—C6B	123.9 (3)
C4A—C5A—C6A	118.1 (3)	C4B—C5B—C6B	118.4 (3)
O1A—C6A—N2A	124.5 (3)	O1B—C6B—N2B	125.0 (3)
O1A—C6A—C5A	121.4 (3)	O1B—C6B—C5B	121.7 (3)
N2A—C6A—C5A	114.2 (3)	N2B—C6B—C5B	113.3 (3)
N3A—C7A—C8A	122.7 (3)	N3B—C7B—C8B	121.3 (4)
N3A—C7A—H7AA	118.7	N3B—C7B—H7BA	119.4
C8A—C7A—H7AA	118.7	C8B—C7B—H7BA	119.4
C9A—C8A—C7A	117.0 (4)	C9B—C8B—C7B	118.8 (4)
C9A—C8A—C12A	123.9 (4)	C9B—C8B—C12B	122.6 (4)
C7A—C8A—C12A	119.1 (3)	C7B—C8B—C12B	118.4 (4)
C8A—C9A—C10A	127.5 (4)	C8B—C9B—C10B	128.5 (5)
C8A—C9A—H9AA	116.3	C8B—C9B—H9BA	115.8
C10A—C9A—H9AA	116.3	C10B—C9B—H9BA	115.8
C9A—C10A—C11A	112.0 (5)	C11B—C10B—C9B	112.3 (6)
C9A—C10A—H10A	109.2	C11B—C10B—H10C	109.1
C11A—C10A—H10A	109.2	C9B—C10B—H10C	109.1
C9A—C10A—H10B	109.2	C11B—C10B—H10D	109.1
C11A—C10A—H10B	109.2	C9B—C10B—H10D	109.1
H10A—C10A—H10B	107.9	H10C—C10B—H10D	107.9
C10A—C11A—H11A	109.5	C10B—C11B—H11D	109.5
C10A—C11A—H11B	109.5	C10B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
C10A—C11A—H11C	109.5	C10B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
C8A—C12A—H12A	109.5	C8B—C12B—H12D	109.5
C8A—C12A—H12B	109.5	C8B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C8A—C12A—H12C	109.5	C8B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5

C6A—N2A—N3A—C7A	−179.9 (3)	C6B—N2B—N3B—C7B	−175.0 (4)
C3A—N1A—C2A—C1A	−0.3 (6)	C3B—N1B—C2B—C1B	−0.3 (7)
C5A—C1A—C2A—N1A	0.4 (6)	C5B—C1B—C2B—N1B	−0.2 (6)
C2A—N1A—C3A—C4A	0.7 (7)	C2B—N1B—C3B—C4B	1.1 (9)
N1A—C3A—C4A—C5A	−1.3 (8)	N1B—C3B—C4B—C5B	−1.5 (10)
C2A—C1A—C5A—C4A	−0.9 (6)	C2B—C1B—C5B—C4B	−0.2 (6)
C2A—C1A—C5A—C6A	−177.8 (3)	C2B—C1B—C5B—C6B	−177.4 (4)
C3A—C4A—C5A—C1A	1.3 (7)	C3B—C4B—C5B—C1B	0.9 (8)
C3A—C4A—C5A—C6A	178.4 (4)	C3B—C4B—C5B—C6B	178.3 (5)
N3A—N2A—C6A—O1A	−3.1 (6)	N3B—N2B—C6B—O1B	0.6 (6)
N3A—N2A—C6A—C5A	176.2 (3)	N3B—N2B—C6B—C5B	−178.2 (3)
C1A—C5A—C6A—O1A	157.8 (4)	C1B—C5B—C6B—O1B	153.4 (4)
C4A—C5A—C6A—O1A	−19.2 (6)	C4B—C5B—C6B—O1B	−23.8 (6)
C1A—C5A—C6A—N2A	−21.5 (5)	C1B—C5B—C6B—N2B	−27.8 (5)
C4A—C5A—C6A—N2A	161.5 (4)	C4B—C5B—C6B—N2B	155.0 (4)
N2A—N3A—C7A—C8A	−179.5 (4)	N2B—N3B—C7B—C8B	−174.3 (4)
N3A—C7A—C8A—C9A	177.8 (4)	N3B—C7B—C8B—C9B	166.8 (6)
N3A—C7A—C8A—C12A	−2.5 (6)	N3B—C7B—C8B—C12B	−7.8 (7)
C7A—C8A—C9A—C10A	−177.9 (5)	C7B—C8B—C9B—C10B	−176.0 (6)
C12A—C8A—C9A—C10A	2.4 (8)	C12B—C8B—C9B—C10B	−1.7 (11)
C8A—C9A—C10A—C11A	127.7 (6)	C8B—C9B—C10B—C11B	−144.2 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2B—H1NB···N1Aⁱ	0.95 (6)	2.08 (6)	2.973 (5)	156 (5)
N2A—H1NA···N1Bⁱⁱ	0.83 (6)	2.26 (6)	3.005 (5)	148 (5)
C7B—H7BA···O1Aⁱⁱⁱ	0.93	2.51	3.171 (5)	129
C12A—H12B···O1B	0.96	2.48	3.433 (5)	173

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) x, −y+2, z−1/2; (iii) x−1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅N₃O
M_r	217.27
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	19.809 (4), 8.3459 (15), 16.021 (3)
β (°)	119.825 (3)
V (Å³)	2297.7 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.54 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.957, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	12644, 3396, 2883
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.225, 1.03
No. of reflections	3396
No. of parameters	301
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.15, −0.47

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2B—H1NB···N1Aⁱ	0.95 (6)	2.08 (6)	2.973 (5)	156 (5)
N2A—H1NA···N1Bⁱⁱ	0.83 (6)	2.26 (6)	3.005 (5)	148 (5)
C7B—H7BA···O1Aⁱⁱⁱ	0.9300	2.5100	3.171 (5)	129.00
C12A—H12B···O1B	0.9600	2.4800	3.433 (5)	173.00

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) x, −y+2, z−1/2; (iii) x−1/2, y+1/2, z.

Footnotes

‡Additional correspondence author, e-mail: amirin@usm.my.

§Thomson Reuters ResearcherID: C-7581-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

This research was supported by Universiti Sains Malaysia (USM) under the Fundamental Research Grant Scheme (203/PFARMASI/671157). HKF and WSL thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). HSN and WSL are also grateful for the award of USM fellowships.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Janin, Y. L. (2007). Bioorg. Med. Chem. 15, 2479–2513. Web of Science CrossRef PubMed CAS Google Scholar
Kahwa, I. A., Selbin, J., Hsieh, T. C.-Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185. CrossRef CAS Web of Science Google Scholar
Lourenco, M. C. S., Ferreira, M. L., de Souza, M. V. N., Peralta, M. A., Vasconcelos, T. R. A. & Henriques, M. G. M. O. (2008). Eur. J. Med. Chem. 43, 1344–1347. Web of Science CrossRef PubMed CAS Google Scholar
Maccari, R., Ottana, R. & Vigorita, M. G. (2005). Bioorg. Med. Chem. Lett. 15, 2509–2513. Web of Science CrossRef PubMed CAS Google Scholar
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Loh, W.-S. & Fun, H.-K. (2009). Acta Cryst. E65, o2540–o2541. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Quah, C. K. & Fun, H.-K. (2010). Acta Cryst. E66, o291. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o579. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, J. (2005). Acta Cryst. E61, o3933–o3934. Web of Science CSD CrossRef IUCr Journals Google Scholar
Slayden, R. A. & Barry, C. E. (2000). Microbes Infect. 2, 659–669. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar