N′-(Cyclo­hexyl­carbon­yl)isonicotino­hydrazide

Naveenkumar, H.S.; Sadikun, A.; Ibrahim, P.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536809027469

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1912

doi:10.1107/S1600536809027469

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N′-(Cyclohexylcarbonyl)isonicotinohydrazide

H. S. Naveenkumar,^a Amirin Sadikun,^a ‡ Pazilah Ibrahim,^a Chin Sing Yeap ^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 7 July 2009; accepted 13 July 2009; online 18 July 2009)

In the title compound, C₁₃H₁₇N₃O₂, the mean plane of the cyclohexane ring forms a dihedral angle of 33.12 (5)° with the pyridine ring. The two O atoms are twisted away from each other, as indicated by the C—N—N—C torsion angle of −74.97 (9)°. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds. The structure is also stabilized by C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For applications of isoniazid derivatives, see: Janin (2007 ); Maccari et al. (2005 ); Slayden & Barry (2000 ). For the preparation, see: Besra et al. (1993 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₁₇N₃O₂
M_r = 247.30
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1184 (2) Å
b = 11.5989 (2) Å
c = 12.1684 (2) Å
V = 1286.97 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.60 × 0.40 × 0.33 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.941, T_max = 0.971
27969 measured reflections
3210 independent reflections
3124 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.084
S = 1.11
3210 reflections
231 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1ⁱ	0.911 (18)	2.095 (18)	2.9456 (10)	155.0 (16)
N3—H1N3⋯O2ⁱⁱ	0.900 (16)	1.854 (16)	2.7486 (9)	172.4 (14)
C2—H2⋯O1ⁱⁱⁱ	1.017 (18)	2.527 (18)	3.4971 (11)	159.4 (14)
C4—H4⋯O1^iv	0.948 (15)	2.502 (15)	3.3062 (10)	142.6 (12)
C10—H10B⋯Cg1^v	1.01 (2)	2.78 (3)	3.7299 (14)	157.1 (16)
C13—H13A⋯Cg1^vi	0.993 (15)	2.958 (16)	3.7039 (10)	132.7 (12)
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+2]$ ; (iv) $[-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (v) $[-x-1, y+{\script{3\over 2}}, -z+{\script{5\over 2}}]$ ; (vi) $[-x+{\script{3\over 2}}, -y+2, z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C1/C2/N1/C3–C5 ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: 10.1107/S1600536809027469/kj2133sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027469/kj2133Isup2.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 & Barry, 2000). As a part of a current work of synthesis of such derivatives, in this paper we present the crystal structure of the title compound which was synthesized in our lab.

Bond lengths and angles of the title compound (I), (Fig. 1) are within the normal range (Allen et al., 1987). The mean plane of cyclohexane ring forms dihedral angle of 33.12 (5)° with the pyridine ring. The O1 and O2 atoms are twisted away from each other as is indicated by torsion angle C6–N2–N3–C7 [-74.97 (9)°]. In the crystal structure, the molecules are linked into three-dimensional network by the intermolecular N2—H1N2···N1, N3—H1N3···O2, C2—H2···O1 and C4—H4···O1 hydrogen bonds. The structure is also stabilized by C—H···π interactions (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000). For the preparation, see: Besra et al. (1993). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of the C1/C2/N1/C3–C5 ring.

Experimental top

The isoniazid (INH) derivative was prepared following the procedure by literature (Besra et al., 1993). Dry dichloromethane (30 ml) and 4-dimethylaminopyridine (4-DMAP) (1.2 eq) was added to cyclohexane carbonyl chloride followed by INH (1.1 eq). The reaction mixture was kept in an ice bath for 1 h and then left stirring under nitrogen overnight at room temperature. Dichloromethane (20 ml) was added to the reaction mixture, which was then washed with water, and the organic layer dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure to afford the crude product which was purified by column chromatography and recrystallized from methanol to afford colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 with atom labels and 50% probability ellipsoids for non-H atoms.

N'-(Cyclohexylcarbonyl)isonicotinohydrazide top

Crystal data top

C₁₃H₁₇N₃O₂	F(000) = 528
M_r = 247.30	D_x = 1.276 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9922 reflections
a = 9.1184 (2) Å	θ = 2.8–35.1°
b = 11.5989 (2) Å	µ = 0.09 mm⁻¹
c = 12.1684 (2) Å	T = 100 K
V = 1286.97 (4) Å³	Block, colourless
Z = 4	0.60 × 0.40 × 0.33 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3210 independent reflections
Radiation source: fine-focus sealed tube	3124 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 35.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
T_min = 0.941, T_max = 0.971	k = −18→17
27969 measured reflections	l = −19→19

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0593P)² + 0.0754P] where P = (F_o² + 2F_c²)/3
3210 reflections	(Δ/σ)_max < 0.001
231 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₃H₁₇N₃O₂	V = 1286.97 (4) Å³
M_r = 247.30	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.1184 (2) Å	µ = 0.09 mm⁻¹
b = 11.5989 (2) Å	T = 100 K
c = 12.1684 (2) Å	0.60 × 0.40 × 0.33 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3210 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3124 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.971	R_int = 0.022
27969 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.25 e Å⁻³
3210 reflections	Δρ_min = −0.34 e Å⁻³
231 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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 > 2sigma(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
O1	0.75737 (8)	1.01913 (6)	1.03928 (5)	0.02041 (13)
O2	0.99005 (6)	0.79925 (5)	1.04401 (5)	0.01593 (11)
N1	1.02861 (8)	1.26064 (6)	0.76325 (6)	0.01714 (12)
N2	0.80178 (7)	0.89033 (6)	0.90156 (5)	0.01293 (11)
N3	0.76418 (7)	0.79834 (6)	0.96907 (5)	0.01347 (11)
C1	0.94236 (10)	1.18220 (7)	0.93422 (6)	0.01703 (14)
C2	1.01495 (11)	1.26604 (7)	0.87318 (7)	0.01889 (14)
C3	0.96940 (10)	1.16932 (7)	0.71250 (6)	0.01606 (13)
C4	0.89624 (9)	1.08036 (7)	0.76639 (6)	0.01426 (12)
C5	0.88303 (8)	1.08714 (6)	0.88042 (6)	0.01264 (12)
C6	0.80847 (8)	0.99670 (6)	0.94875 (6)	0.01322 (12)
C7	0.86549 (7)	0.75756 (6)	1.04018 (6)	0.01175 (11)
C8	0.81852 (8)	0.65554 (6)	1.10913 (6)	0.01238 (11)
C9	0.87614 (11)	0.54417 (7)	1.05682 (7)	0.02033 (15)
C10	0.83192 (15)	0.43958 (8)	1.12611 (10)	0.0300 (2)
C11	0.88525 (14)	0.45089 (10)	1.24449 (11)	0.0315 (2)
C12	0.82967 (13)	0.56214 (10)	1.29578 (7)	0.02597 (18)
C13	0.87382 (11)	0.66737 (8)	1.22748 (7)	0.02036 (15)
H1	0.936 (2)	1.1925 (16)	1.0135 (14)	0.033 (4)*
H2	1.062 (2)	1.3365 (15)	0.9082 (14)	0.032 (4)*
H3	0.9786 (19)	1.1702 (14)	0.6350 (14)	0.027 (4)*
H4	0.8560 (17)	1.0205 (13)	0.7227 (12)	0.018 (3)*
H8	0.7101 (18)	0.6508 (14)	1.1062 (12)	0.021 (3)*
H9A	0.837 (2)	0.5361 (17)	0.9849 (16)	0.042 (5)*
H9B	0.9813 (19)	0.5498 (15)	1.0523 (14)	0.028 (4)*
H10A	0.869 (2)	0.3690 (19)	1.0921 (16)	0.046 (5)*
H10B	0.722 (3)	0.4297 (19)	1.1277 (16)	0.047 (5)*
H11A	0.860 (2)	0.3808 (16)	1.2833 (14)	0.031 (4)*
H11B	0.995 (3)	0.454 (2)	1.249 (2)	0.053 (6)*
H12A	0.872 (2)	0.5711 (18)	1.3708 (15)	0.043 (5)*
H12B	0.722 (2)	0.5602 (16)	1.2991 (13)	0.032 (4)*
H13A	0.8388 (18)	0.7410 (13)	1.2598 (12)	0.018 (3)*
H13B	0.985 (2)	0.6778 (15)	1.2258 (14)	0.030 (4)*
H1N2	0.862 (2)	0.8724 (16)	0.8443 (15)	0.036 (5)*
H1N3	0.6729 (18)	0.7705 (13)	0.9596 (12)	0.022 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0286 (3)	0.0174 (3)	0.0152 (2)	0.0016 (2)	0.0095 (2)	0.0005 (2)
O2	0.0107 (2)	0.0156 (2)	0.0215 (2)	−0.00104 (18)	−0.00008 (19)	0.0012 (2)
N1	0.0205 (3)	0.0136 (2)	0.0173 (3)	−0.0004 (2)	0.0028 (2)	0.0031 (2)
N2	0.0148 (2)	0.0104 (2)	0.0135 (2)	−0.00010 (19)	0.00287 (19)	0.00212 (19)
N3	0.0116 (2)	0.0128 (2)	0.0159 (2)	−0.00129 (19)	−0.0005 (2)	0.0046 (2)
C1	0.0258 (3)	0.0126 (3)	0.0127 (3)	−0.0015 (3)	0.0022 (2)	−0.0006 (2)
C2	0.0263 (4)	0.0129 (3)	0.0175 (3)	−0.0031 (3)	0.0013 (3)	0.0000 (2)
C3	0.0198 (3)	0.0155 (3)	0.0129 (3)	0.0002 (3)	0.0022 (2)	0.0030 (2)
C4	0.0179 (3)	0.0133 (3)	0.0115 (2)	−0.0005 (2)	0.0009 (2)	0.0011 (2)
C5	0.0158 (3)	0.0107 (3)	0.0115 (2)	0.0009 (2)	0.0018 (2)	0.0012 (2)
C6	0.0149 (3)	0.0116 (3)	0.0131 (3)	0.0016 (2)	0.0026 (2)	0.0014 (2)
C7	0.0111 (2)	0.0111 (2)	0.0131 (2)	0.0007 (2)	0.0008 (2)	−0.0001 (2)
C8	0.0125 (2)	0.0115 (3)	0.0131 (3)	0.0003 (2)	0.0005 (2)	0.0015 (2)
C9	0.0292 (4)	0.0117 (3)	0.0202 (3)	−0.0009 (3)	0.0069 (3)	−0.0015 (2)
C10	0.0457 (6)	0.0107 (3)	0.0336 (5)	−0.0014 (4)	0.0128 (4)	0.0013 (3)
C11	0.0324 (5)	0.0236 (4)	0.0386 (5)	0.0063 (4)	0.0018 (4)	0.0171 (4)
C12	0.0337 (5)	0.0278 (4)	0.0164 (3)	−0.0030 (4)	−0.0022 (3)	0.0080 (3)
C13	0.0275 (4)	0.0196 (3)	0.0139 (3)	−0.0032 (3)	−0.0030 (3)	0.0010 (2)

Geometric parameters (Å, º) top

O1—C6	1.2241 (9)	C7—C8	1.5125 (10)
O2—C7	1.2353 (9)	C8—C13	1.5321 (11)
N1—C3	1.3397 (11)	C8—C9	1.5329 (11)
N1—C2	1.3448 (11)	C8—H8	0.990 (16)
N2—C6	1.3622 (10)	C9—C10	1.5315 (13)
N2—N3	1.3895 (9)	C9—H9A	0.95 (2)
N2—H1N2	0.910 (19)	C9—H9B	0.963 (18)
N3—C7	1.3513 (9)	C10—C11	1.5260 (19)
N3—H1N3	0.900 (17)	C10—H10A	0.98 (2)
C1—C2	1.3912 (11)	C10—H10B	1.01 (2)
C1—C5	1.3917 (11)	C11—C12	1.5203 (18)
C1—H1	0.973 (18)	C11—H11A	0.967 (19)
C2—H2	1.017 (18)	C11—H11B	1.00 (3)
C3—C4	1.3927 (11)	C12—C13	1.5306 (13)
C3—H3	0.946 (17)	C12—H12A	0.997 (19)
C4—C5	1.3950 (10)	C12—H12B	0.98 (2)
C4—H4	0.948 (15)	C13—H13A	0.993 (15)
C5—C6	1.5014 (10)	C13—H13B	1.02 (2)

C3—N1—C2	117.26 (7)	C13—C8—H8	111.5 (8)
C6—N2—N3	117.22 (6)	C9—C8—H8	106.3 (9)
C6—N2—H1N2	120.2 (12)	C10—C9—C8	110.40 (7)
N3—N2—H1N2	115.2 (11)	C10—C9—H9A	109.4 (13)
C7—N3—N2	118.60 (6)	C8—C9—H9A	109.8 (13)
C7—N3—H1N3	126.1 (10)	C10—C9—H9B	110.4 (10)
N2—N3—H1N3	115.3 (10)	C8—C9—H9B	107.9 (11)
C2—C1—C5	119.18 (7)	H9A—C9—H9B	109.0 (17)
C2—C1—H1	118.0 (11)	C11—C10—C9	111.57 (9)
C5—C1—H1	122.8 (11)	C11—C10—H10A	111.1 (12)
N1—C2—C1	122.85 (8)	C9—C10—H10A	109.8 (12)
N1—C2—H2	114.5 (10)	C11—C10—H10B	107.9 (11)
C1—C2—H2	122.6 (10)	C9—C10—H10B	111.2 (12)
N1—C3—C4	124.18 (7)	H10A—C10—H10B	105.1 (17)
N1—C3—H3	114.5 (10)	C12—C11—C10	110.75 (8)
C4—C3—H3	121.3 (10)	C12—C11—H11A	115.7 (11)
C3—C4—C5	117.90 (7)	C10—C11—H11A	108.2 (11)
C3—C4—H4	117.7 (9)	C12—C11—H11B	106.4 (14)
C5—C4—H4	124.4 (9)	C10—C11—H11B	112.2 (15)
C1—C5—C4	118.62 (7)	H11A—C11—H11B	103.5 (18)
C1—C5—C6	117.98 (6)	C11—C12—C13	111.48 (8)
C4—C5—C6	123.41 (7)	C11—C12—H12A	109.6 (12)
O1—C6—N2	123.70 (7)	C13—C12—H12A	108.2 (12)
O1—C6—C5	121.48 (7)	C11—C12—H12B	109.3 (11)
N2—C6—C5	114.82 (6)	C13—C12—H12B	107.7 (11)
O2—C7—N3	121.04 (7)	H12A—C12—H12B	110.6 (16)
O2—C7—C8	123.07 (7)	C12—C13—C8	110.63 (7)
N3—C7—C8	115.81 (6)	C12—C13—H13A	112.7 (9)
C7—C8—C13	110.98 (6)	C8—C13—H13A	110.1 (9)
C7—C8—C9	109.38 (6)	C12—C13—H13B	111.5 (10)
C13—C8—C9	110.67 (7)	C8—C13—H13B	108.6 (9)
C7—C8—H8	107.9 (9)	H13A—C13—H13B	103.0 (14)

C6—N2—N3—C7	−74.97 (9)	N2—N3—C7—O2	−1.43 (11)
C3—N1—C2—C1	−0.37 (13)	N2—N3—C7—C8	−178.54 (6)
C5—C1—C2—N1	1.17 (14)	O2—C7—C8—C13	43.39 (10)
C2—N1—C3—C4	−0.43 (13)	N3—C7—C8—C13	−139.56 (7)
N1—C3—C4—C5	0.40 (13)	O2—C7—C8—C9	−79.00 (9)
C2—C1—C5—C4	−1.15 (12)	N3—C7—C8—C9	98.04 (8)
C2—C1—C5—C6	178.57 (8)	C7—C8—C9—C10	179.16 (8)
C3—C4—C5—C1	0.42 (12)	C13—C8—C9—C10	56.58 (10)
C3—C4—C5—C6	−179.29 (7)	C8—C9—C10—C11	−56.32 (12)
N3—N2—C6—O1	−14.45 (11)	C9—C10—C11—C12	55.80 (13)
N3—N2—C6—C5	166.16 (6)	C10—C11—C12—C13	−55.73 (12)
C1—C5—C6—O1	23.87 (12)	C11—C12—C13—C8	56.45 (11)
C4—C5—C6—O1	−156.42 (8)	C7—C8—C13—C12	−178.34 (7)
C1—C5—C6—N2	−156.72 (7)	C9—C8—C13—C12	−56.70 (10)
C4—C5—C6—N2	22.99 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1ⁱ	0.911 (18)	2.095 (18)	2.9456 (10)	155.0 (16)
N3—H1N3···O2ⁱⁱ	0.900 (16)	1.854 (16)	2.7486 (9)	172.4 (14)
C2—H2···O1ⁱⁱⁱ	1.017 (18)	2.527 (18)	3.4971 (11)	159.4 (14)
C4—H4···O1^iv	0.948 (15)	2.502 (15)	3.3062 (10)	142.6 (12)
C10—H10B···Cg1^v	1.01 (2)	2.78 (3)	3.7299 (14)	157.1 (16)
C13—H13A···Cg1^vi	0.993 (15)	2.958 (16)	3.7039 (10)	132.7 (12)

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, −z+2; (iii) x+1/2, −y+5/2, −z+2; (iv) −x+3/2, −y+2, z−1/2; (v) −x−1, y+3/2, −z+5/2; (vi) −x+3/2, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇N₃O₂
M_r	247.30
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	9.1184 (2), 11.5989 (2), 12.1684 (2)
V (Å³)	1286.97 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.40 × 0.33

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.941, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	27969, 3210, 3124
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.810

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.084, 1.11
No. of reflections	3210
No. of parameters	231
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.34

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
N2—H1N2···N1ⁱ	0.911 (18)	2.095 (18)	2.9456 (10)	155.0 (16)
N3—H1N3···O2ⁱⁱ	0.900 (16)	1.854 (16)	2.7486 (9)	172.4 (14)
C2—H2···O1ⁱⁱⁱ	1.017 (18)	2.527 (18)	3.4971 (11)	159.4 (14)
C4—H4···O1^iv	0.948 (15)	2.502 (15)	3.3062 (10)	142.6 (12)
C10—H10B···Cg1^v	1.01 (2)	2.78 (3)	3.7299 (14)	157.1 (16)
C13—H13A···Cg1^vi	0.993 (15)	2.958 (16)	3.7039 (10)	132.7 (12)

Footnotes

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

§Thomson Reuters ResearcherID: A-5523-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

This research is supported by Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815005). HKF and CSY thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY thanks the Malaysian Government and USM for the award of the post of Research Officer under the Science Fund Grant (No. 305/PFIZIK/613312). HSNK is grateful for a USM fellowship for financial assistance.

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