(E)-N'-(2,3,4-Trimethoxy­benzyl­idene)isonicotinohydrazide

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

doi:10.1107/S1600536810015266

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1231-o1232

https://doi.org/10.1107/S1600536810015266

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(E)-N'-(2,3,4-Trimethoxybenzylidene)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 April 2010; accepted 26 April 2010; online 30 April 2010)

In the title compound, C₁₆H₁₇N₃O₄, the molecule exists in an E configuration with respect to the C=N double bond. The molecule is not planar, the dihedral angle between the pyridine and benzene rings being 71.67 (8)°. In the crystal structure, molecules are linked into chains along the b axis by bifurcated N—H⋯O and C—H⋯O hydrogen bonds. These chains are linked into a three-dimensional network by C—H⋯O and C—H⋯π interactions.

Related literature

For applications of isoniazid derivatives, see: Janin (2007 ); Maccari et al. (2005 ); Slayden & Barry (2000 ); Kahwa et al. (1986 ). For preparation of the compound, see: Lourenco et al. (2008 ). For related structures, see: Naveenkumar et al. (2009 , 2010a ,b ); Shi (2005 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₇N₃O₄
M_r = 315.33
Monoclinic, P 2₁ /c
a = 14.246 (3) Å
b = 9.397 (2) Å
c = 12.098 (3) Å
β = 109.245 (6)°
V = 1529.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.38 × 0.33 × 0.14 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.963, T_max = 0.986
14341 measured reflections
3482 independent reflections
2988 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.159
S = 1.10
3482 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/C2/N1/C3/C4/C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.91 (3)	2.09 (3)	2.7987 (19)	134 (2)
C4—H4A⋯O1ⁱ	0.93	2.46	3.348 (2)	159
C14—H14C⋯O3	0.96	2.55	3.113 (2)	118
C15—H15C⋯O2ⁱⁱ	0.96	2.49	3.292 (2)	141
C16—H16A⋯O3ⁱⁱⁱ	0.96	2.57	3.518 (2)	167
C14—H14B⋯Cg1ⁱ	0.96	2.81	3.719 (3)	159
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) -x+1, -y+1, -z+1.

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/S1600536810015266/tk2657sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015266/tk2657Isup2.hkl

checkCIF report

Comment top

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

The geometric parameters of (I) are comparable to those in related structures (Naveenkumar et al., 2009, 2010a, 2010b; Shi, 2005). The molecule exists in an E configuration with respect to the C7═N3 double bond (Fig. 1). The isoniazid group is twisted away with the torsion angle of C1–C5–C6–N2 being -149.60 (15)°. The dihedral angle between the pyridine ring and the benzene ring is 71.67 (8)°. One of the methoxy group is coplanar with the benzene ring whereas the other two are twisted away from the benzene ring [torsion angles: C16–O4–C11–C12 = -3.8 (2), C15–O3–C10–C11 = -97.83 (17), C14–O2–C9–C10 = 73.23 (19) °]. A weak intramolecular C14–H14C···O3 hydrogen bond stabilizes the molecular structure (Table 1). In the crystal structure, the molecules are linked into one-dimensional chains along the b axis by the bifurcated intermolecular N2–H1N2···O1 and C4–H4A···O1 hydrogen bonds (Table 1). These chains are linked into a three-dimensional network by C15–H15C···O2, C16–H16A···O3 and C14–H14B···Cg1 interactions (Fig. 2, Table 1).

Related literature top

For applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000); Kahwa et al. (1986). For preparation of the compound, see: Lourenco et al. (2008). For related structures, see: Naveenkumar et al. (2009, 2010a,b); Shi (2005). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The isoniazid derivative (I) was prepared following the procedure by Lourenco et al. (2008). 2,3,4-Trimethoxybenzaldehyde (1.0 eq) was reacted with isoniazid (1.0 eq) in ethanol/water. After stirring for 3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue was purified by washing with cold ethanol and ethyl ether, affording the pure derivative. The colourless crystals were obtained by recrystallization from a methanol solution of (I).

Structure description top

For applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000); Kahwa et al. (1986). For preparation of the compound, see: Lourenco et al. (2008). For related structures, see: Naveenkumar et al. (2009, 2010a,b); Shi (2005). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

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 (I) with atom labels and 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of (I), viewed down the c axis, showing the molecules are linked into a 3-D network. Intermolecular contacts are shown as dashed lines.

(E)-N'-(2,3,4-Trimethoxybenzylidene)isonicotinohydrazide top

Crystal data top

C₁₆H₁₇N₃O₄	F(000) = 664
M_r = 315.33	D_x = 1.370 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5847 reflections
a = 14.246 (3) Å	θ = 2.8–33.0°
b = 9.397 (2) Å	µ = 0.10 mm⁻¹
c = 12.098 (3) Å	T = 100 K
β = 109.245 (6)°	Block, colourless
V = 1529.1 (6) Å³	0.38 × 0.33 × 0.14 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3482 independent reflections
Radiation source: fine-focus sealed tube	2988 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→18
T_min = 0.963, T_max = 0.986	k = −11→12
14341 measured reflections	l = −15→15

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0903P)² + 0.7464P] where P = (F_o² + 2F_c²)/3
3482 reflections	(Δ/σ)_max < 0.001
215 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₆H₁₇N₃O₄	V = 1529.1 (6) Å³
M_r = 315.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.246 (3) Å	µ = 0.10 mm⁻¹
b = 9.397 (2) Å	T = 100 K
c = 12.098 (3) Å	0.38 × 0.33 × 0.14 mm
β = 109.245 (6)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3482 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2988 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.986	R_int = 0.030
14341 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.57 e Å⁻³
3482 reflections	Δρ_min = −0.38 e Å⁻³
215 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 > 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	0.01090 (9)	0.86823 (12)	−0.28320 (11)	0.0286 (3)
O2	0.36424 (9)	0.41851 (12)	−0.00731 (10)	0.0232 (3)
O3	0.47223 (8)	0.40332 (13)	0.23303 (10)	0.0235 (3)
O4	0.41436 (9)	0.55428 (13)	0.38640 (10)	0.0245 (3)
N1	−0.18863 (12)	0.63126 (17)	−0.66119 (13)	0.0302 (4)
N2	0.05989 (10)	0.63755 (14)	−0.24901 (12)	0.0207 (3)
N3	0.11895 (10)	0.66421 (14)	−0.13400 (11)	0.0208 (3)
C1	−0.08316 (12)	0.79807 (18)	−0.52380 (15)	0.0238 (3)
H1A	−0.0557	0.8888	−0.5098	0.029*
C2	−0.14580 (13)	0.76010 (19)	−0.63502 (15)	0.0277 (4)
H2A	−0.1587	0.8275	−0.6944	0.033*
C3	−0.16847 (13)	0.53782 (19)	−0.57329 (15)	0.0278 (4)
H3A	−0.1983	0.4487	−0.5894	0.033*
C4	−0.10626 (12)	0.56370 (17)	−0.45947 (15)	0.0231 (3)
H4A	−0.0942	0.4937	−0.4021	0.028*
C5	−0.06239 (11)	0.69824 (17)	−0.43404 (14)	0.0204 (3)
C6	0.00512 (11)	0.74314 (16)	−0.31422 (14)	0.0203 (3)
C7	0.18304 (11)	0.56473 (17)	−0.09093 (13)	0.0200 (3)
H7A	0.1910	0.4914	−0.1387	0.024*
C8	0.24315 (11)	0.56734 (16)	0.03316 (14)	0.0198 (3)
C9	0.33100 (11)	0.48599 (16)	0.07346 (13)	0.0184 (3)
C10	0.38660 (11)	0.48299 (16)	0.19251 (13)	0.0188 (3)
C11	0.35435 (12)	0.56152 (17)	0.27246 (14)	0.0205 (3)
C12	0.26610 (12)	0.63962 (17)	0.23309 (15)	0.0233 (3)
H12A	0.2438	0.6895	0.2860	0.028*
C13	0.21207 (12)	0.64218 (17)	0.11454 (14)	0.0229 (3)
H13A	0.1537	0.6951	0.0886	0.027*
C14	0.35843 (15)	0.26623 (19)	−0.00823 (17)	0.0325 (4)
H14A	0.3768	0.2297	−0.0723	0.049*
H14B	0.2917	0.2376	−0.0171	0.049*
H14C	0.4029	0.2294	0.0641	0.049*
C15	0.55771 (13)	0.4749 (2)	0.22131 (17)	0.0324 (4)
H15A	0.6152	0.4152	0.2516	0.049*
H15B	0.5682	0.5626	0.2644	0.049*
H15C	0.5468	0.4945	0.1401	0.049*
C16	0.38727 (14)	0.6398 (2)	0.46951 (15)	0.0308 (4)
H16A	0.4343	0.6248	0.5463	0.046*
H16B	0.3221	0.6132	0.4690	0.046*
H16C	0.3873	0.7384	0.4488	0.046*
H1N2	0.0529 (18)	0.544 (3)	−0.270 (2)	0.038 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0297 (6)	0.0180 (6)	0.0300 (6)	0.0029 (5)	−0.0011 (5)	−0.0029 (5)
O2	0.0270 (6)	0.0225 (6)	0.0204 (6)	0.0008 (4)	0.0083 (5)	−0.0008 (4)
O3	0.0192 (6)	0.0264 (6)	0.0232 (6)	0.0059 (4)	0.0047 (4)	0.0030 (4)
O4	0.0264 (6)	0.0278 (6)	0.0176 (6)	0.0044 (5)	0.0048 (5)	−0.0011 (4)
N1	0.0324 (8)	0.0321 (8)	0.0239 (7)	0.0010 (6)	0.0062 (6)	−0.0048 (6)
N2	0.0224 (7)	0.0167 (6)	0.0202 (6)	0.0005 (5)	0.0032 (5)	−0.0022 (5)
N3	0.0217 (6)	0.0189 (6)	0.0200 (6)	−0.0027 (5)	0.0045 (5)	−0.0024 (5)
C1	0.0234 (7)	0.0205 (8)	0.0288 (8)	0.0018 (6)	0.0104 (6)	0.0013 (6)
C2	0.0306 (9)	0.0289 (9)	0.0244 (8)	0.0040 (7)	0.0101 (7)	0.0026 (6)
C3	0.0276 (8)	0.0244 (8)	0.0285 (8)	−0.0007 (7)	0.0055 (7)	−0.0062 (7)
C4	0.0214 (7)	0.0200 (8)	0.0272 (8)	0.0014 (6)	0.0071 (6)	0.0000 (6)
C5	0.0181 (7)	0.0197 (7)	0.0243 (8)	0.0031 (6)	0.0080 (6)	−0.0013 (6)
C6	0.0178 (7)	0.0172 (7)	0.0257 (8)	0.0011 (6)	0.0069 (6)	−0.0006 (6)
C7	0.0201 (7)	0.0191 (7)	0.0201 (7)	−0.0028 (6)	0.0054 (6)	−0.0004 (5)
C8	0.0192 (7)	0.0175 (7)	0.0211 (7)	−0.0023 (6)	0.0044 (6)	0.0028 (5)
C9	0.0198 (7)	0.0160 (7)	0.0197 (7)	−0.0020 (5)	0.0069 (6)	0.0004 (5)
C10	0.0175 (7)	0.0170 (7)	0.0212 (7)	0.0014 (5)	0.0054 (6)	0.0021 (5)
C11	0.0222 (7)	0.0195 (7)	0.0192 (7)	−0.0006 (6)	0.0059 (6)	0.0013 (6)
C12	0.0242 (8)	0.0227 (8)	0.0236 (8)	0.0035 (6)	0.0088 (6)	−0.0016 (6)
C13	0.0216 (7)	0.0199 (8)	0.0259 (8)	0.0026 (6)	0.0061 (6)	0.0019 (6)
C14	0.0394 (10)	0.0229 (9)	0.0378 (10)	0.0001 (7)	0.0165 (8)	−0.0068 (7)
C15	0.0205 (8)	0.0433 (11)	0.0336 (9)	0.0019 (7)	0.0092 (7)	0.0000 (8)
C16	0.0330 (9)	0.0381 (10)	0.0211 (8)	0.0055 (8)	0.0086 (7)	−0.0035 (7)

Geometric parameters (Å, º) top

O1—C6	1.228 (2)	C5—C6	1.512 (2)
O2—C9	1.3733 (19)	C7—C8	1.463 (2)
O2—C14	1.433 (2)	C7—H7A	0.9300
O3—C10	1.3765 (18)	C8—C13	1.395 (2)
O3—C15	1.438 (2)	C8—C9	1.409 (2)
O4—C11	1.3634 (19)	C9—C10	1.397 (2)
O4—C16	1.436 (2)	C10—C11	1.409 (2)
N1—C3	1.335 (2)	C11—C12	1.397 (2)
N1—C2	1.346 (2)	C12—C13	1.387 (2)
N2—C6	1.345 (2)	C12—H12A	0.9300
N2—N3	1.3910 (18)	C13—H13A	0.9300
N2—H1N2	0.91 (3)	C14—H14A	0.9600
N3—C7	1.290 (2)	C14—H14B	0.9600
C1—C5	1.391 (2)	C14—H14C	0.9600
C1—C2	1.394 (2)	C15—H15A	0.9600
C1—H1A	0.9300	C15—H15B	0.9600
C2—H2A	0.9300	C15—H15C	0.9600
C3—C4	1.391 (2)	C16—H16A	0.9600
C3—H3A	0.9300	C16—H16B	0.9600
C4—C5	1.399 (2)	C16—H16C	0.9600
C4—H4A	0.9300

C9—O2—C14	115.72 (13)	O2—C9—C8	118.64 (14)
C10—O3—C15	112.99 (13)	C10—C9—C8	120.32 (14)
C11—O4—C16	117.16 (13)	O3—C10—C9	120.87 (14)
C3—N1—C2	116.26 (15)	O3—C10—C11	119.46 (13)
C6—N2—N3	119.77 (13)	C9—C10—C11	119.68 (14)
C6—N2—H1N2	124.0 (15)	O4—C11—C12	124.39 (15)
N3—N2—H1N2	115.3 (15)	O4—C11—C10	115.49 (14)
C7—N3—N2	112.81 (13)	C12—C11—C10	120.11 (15)
C5—C1—C2	119.00 (16)	C13—C12—C11	119.48 (15)
C5—C1—H1A	120.5	C13—C12—H12A	120.3
C2—C1—H1A	120.5	C11—C12—H12A	120.3
N1—C2—C1	123.62 (16)	C12—C13—C8	121.61 (15)
N1—C2—H2A	118.2	C12—C13—H13A	119.2
C1—C2—H2A	118.2	C8—C13—H13A	119.2
N1—C3—C4	124.95 (16)	O2—C14—H14A	109.5
N1—C3—H3A	117.5	O2—C14—H14B	109.5
C4—C3—H3A	117.5	H14A—C14—H14B	109.5
C3—C4—C5	117.92 (16)	O2—C14—H14C	109.5
C3—C4—H4A	121.0	H14A—C14—H14C	109.5
C5—C4—H4A	121.0	H14B—C14—H14C	109.5
C1—C5—C4	118.23 (15)	O3—C15—H15A	109.5
C1—C5—C6	117.70 (15)	O3—C15—H15B	109.5
C4—C5—C6	124.06 (15)	H15A—C15—H15B	109.5
O1—C6—N2	123.99 (15)	O3—C15—H15C	109.5
O1—C6—C5	121.16 (14)	H15A—C15—H15C	109.5
N2—C6—C5	114.79 (14)	H15B—C15—H15C	109.5
N3—C7—C8	119.94 (14)	O4—C16—H16A	109.5
N3—C7—H7A	120.0	O4—C16—H16B	109.5
C8—C7—H7A	120.0	H16A—C16—H16B	109.5
C13—C8—C9	118.77 (14)	O4—C16—H16C	109.5
C13—C8—C7	121.20 (14)	H16A—C16—H16C	109.5
C9—C8—C7	119.90 (14)	H16B—C16—H16C	109.5
O2—C9—C10	120.87 (13)

C6—N2—N3—C7	−165.58 (14)	C7—C8—C9—O2	7.4 (2)
C3—N1—C2—C1	0.3 (3)	C13—C8—C9—C10	−1.2 (2)
C5—C1—C2—N1	0.5 (3)	C7—C8—C9—C10	−177.24 (14)
C2—N1—C3—C4	−1.0 (3)	C15—O3—C10—C9	82.69 (18)
N1—C3—C4—C5	1.0 (3)	C15—O3—C10—C11	−97.83 (17)
C2—C1—C5—C4	−0.5 (2)	O2—C9—C10—O3	−5.1 (2)
C2—C1—C5—C6	−179.50 (14)	C8—C9—C10—O3	179.63 (14)
C3—C4—C5—C1	−0.2 (2)	O2—C9—C10—C11	175.45 (14)
C3—C4—C5—C6	178.75 (15)	C8—C9—C10—C11	0.2 (2)
N3—N2—C6—O1	7.8 (2)	C16—O4—C11—C12	−3.8 (2)
N3—N2—C6—C5	−175.09 (13)	C16—O4—C11—C10	176.28 (14)
C1—C5—C6—O1	27.6 (2)	O3—C10—C11—O4	1.7 (2)
C4—C5—C6—O1	−151.38 (17)	C9—C10—C11—O4	−178.79 (13)
C1—C5—C6—N2	−149.60 (15)	O3—C10—C11—C12	−178.17 (14)
C4—C5—C6—N2	31.5 (2)	C9—C10—C11—C12	1.3 (2)
N2—N3—C7—C8	−172.80 (13)	O4—C11—C12—C13	178.42 (15)
N3—C7—C8—C13	22.4 (2)	C10—C11—C12—C13	−1.7 (2)
N3—C7—C8—C9	−161.70 (15)	C11—C12—C13—C8	0.6 (2)
C14—O2—C9—C10	73.23 (19)	C9—C8—C13—C12	0.8 (2)
C14—O2—C9—C8	−111.40 (16)	C7—C8—C13—C12	176.81 (15)
C13—C8—C9—O2	−176.62 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is centroid of the C1/C2/N1/C3/C4/C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.91 (3)	2.09 (3)	2.7987 (19)	134 (2)
C4—H4A···O1ⁱ	0.93	2.46	3.348 (2)	159
C14—H14C···O3	0.96	2.55	3.113 (2)	118
C15—H15C···O2ⁱⁱ	0.96	2.49	3.292 (2)	141
C16—H16A···O3ⁱⁱⁱ	0.96	2.57	3.518 (2)	167
C14—H14B···Cg1ⁱ	0.96	2.81	3.719 (3)	159

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O₄
M_r	315.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.246 (3), 9.397 (2), 12.098 (3)
β (°)	109.245 (6)
V (Å³)	1529.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.38 × 0.33 × 0.14

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.963, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	14341, 3482, 2988
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.159, 1.10
No. of reflections	3482
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.38

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

Hydrogen-bond geometry (Å, º) top

Cg1 is centroid of the C1/C2/N1/C3/C4/C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.91 (3)	2.09 (3)	2.7987 (19)	134 (2)
C4—H4A···O1ⁱ	0.93	2.46	3.348 (2)	159
C14—H14C···O3	0.96	2.55	3.113 (2)	118
C15—H15C···O2ⁱⁱ	0.96	2.49	3.292 (2)	141
C16—H16A···O3ⁱⁱⁱ	0.96	2.57	3.518 (2)	167
C14—H14B···Cg1ⁱ	0.96	2.81	3.719 (3)	159

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

Footnotes

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

§Thomson Reuters ResearcherID: A-5523-2009.

¶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). HSNK and CSY are grateful to USM for USM Fellowships. HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012).

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