(E)-N′-(3-Benz­yloxy-4-methoxy­benzyl­idene)isonicotinohydrazide

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

doi:10.1107/S1600536809037921

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2540-o2541

doi:10.1107/S1600536809037921

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(E)-N′-(3-Benzyloxy-4-methoxybenzylidene)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 18 September 2009; accepted 19 September 2009; online 26 September 2009)

In the title compound, C₂₁H₁₉N₃O₃, the pyridine ring forms a dihedral angle of 15.25 (6)° with the benzene ring. The dihedral angle between the two benzene rings is 83.66 (7)°. The methoxy group is slightly twisted away from the attached ring [C—O—C—C = 7.5 (2)°]. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N—H⋯N and C—H⋯O hydrogen bonds. The structure is further 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: Lourenço et al. (2008 ). For the biological activity of Schiff bases, see: Kahwa et al. (1986 ). For related structures, see: Naveenkumar, Sadikun, Ibrahim, Goh & Fun (2009 ); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2009 ); Shi (2005 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₁₉N₃O₃
M_r = 361.39
Monoclinic, P 2₁ /c
a = 18.3930 (6) Å
b = 11.5574 (4) Å
c = 8.3508 (3) Å
β = 93.436 (2)°
V = 1771.98 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.71 × 0.13 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.937, T_max = 0.992
27863 measured reflections
6434 independent reflections
3841 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.145
S = 1.06
6433 reflections
249 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1ⁱ	0.88 (2)	2.54 (2)	3.3122 (17)	146 (1)
C9—H9A⋯O1ⁱⁱ	0.93	2.55	3.3524 (17)	144
C19—H19A⋯O3ⁱⁱⁱ	0.93	2.54	3.3960 (17)	153
C17—H17A⋯Cg1^iv	0.93	2.93	3.6694 (17)	137
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y+2, -z+1; (iv) x, y, z+1.

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/S1600536809037921/ci2917sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037921/ci2917Isup2.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). 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-benzylidene) isonicotinohydrazide derivatives, in this paper we present the crystal structure of the title compound.

Bond lengths (Allen et al., 1987) and the angles of the title compound (Fig. 1) are within the normal range and are comparable to those observed for closely related structures (Naveenkumar, Sadikun, Ibrahim, Goh & Fun, 2009; Naveenkumar, Sadikun, Ibrahim, Yeap & Fun, 2009). The mean plane of pyridine (C1–C5/N1) ring forms a dihedral angle of 15.25 (6)° with the benzene (C8–C13) ring. The two benzene (C8–C13 and C15–C20) rings form a dihedral angle of 83.66 (7)° with each other.

In the crystal packing (Fig. 2), molecules are linked into a three-dimensional network by intermolecular N2—H1N2···N1, C9—H9A···O1 and C19—H19A···O3 hydrogen bonds. The crystal structure is further stabilized by C17—H17A···Cg1 interactions (Table 1; Cg1 is the centroid of the C8-C13 benzene ring).

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: Lourenço et al. (2008). For the biological activity of Schiff bases, see: Kahwa et al. (1986). For related structures, see: Naveenkumar, Sadikun, Ibrahim, Goh & Fun (2009); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2009); Shi (2005). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The isoniazid (INH) derivative was prepared following the procedure by literature (Lourenço et al., 2008). (E)—N'-(3-Benzyloxy-4-methoxybenzylidene)isonicotinohydrazide was prepared by reaction between the 3-benzyloxy-4-methoxy benzaldehyde (1.0 eq) with INH (1.0 eq) in ethanol/water (10 ml), initially dissolving the INH in water and adding the respective solution over a solution of the aldehyde in ethanol. After stirring for 1 to 3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue was purified by washing with cold ethyl alcohol and ethyl ether to afford the pure derivative. Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of a dimethyl sulfoxide solution at room temperature.

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, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

(E)-N'-(3-Benzyloxy-4-methoxybenzylidene)isonicotinohydrazide top

Crystal data top

C₂₁H₁₉N₃O₃	F(000) = 760
M_r = 361.39	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4601 reflections
a = 18.3930 (6) Å	θ = 2.8–32.1°
b = 11.5574 (4) Å	µ = 0.09 mm⁻¹
c = 8.3508 (3) Å	T = 100 K
β = 93.436 (2)°	Needle, yellow
V = 1771.98 (11) Å³	0.71 × 0.13 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6434 independent reflections
Radiation source: fine-focus sealed tube	3841 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 32.6°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −26→27
T_min = 0.937, T_max = 0.992	k = −15→17
27863 measured reflections	l = −12→12

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0618P)²] where P = (F_o² + 2F_c²)/3
6433 reflections	(Δ/σ)_max = 0.001
249 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₁H₁₉N₃O₃	V = 1771.98 (11) Å³
M_r = 361.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.3930 (6) Å	µ = 0.09 mm⁻¹
b = 11.5574 (4) Å	T = 100 K
c = 8.3508 (3) Å	0.71 × 0.13 × 0.09 mm
β = 93.436 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6434 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3841 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.992	R_int = 0.061
27863 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.37 e Å⁻³
6433 reflections	Δρ_min = −0.28 e Å⁻³
249 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 > 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
O1	0.34254 (5)	0.51645 (9)	0.11366 (12)	0.0270 (2)
O2	0.17576 (5)	0.99561 (8)	0.38579 (11)	0.0206 (2)
O3	0.17536 (5)	1.19805 (8)	0.25594 (11)	0.0221 (2)
N1	0.49029 (7)	0.30387 (11)	−0.27715 (14)	0.0258 (3)
N2	0.38144 (6)	0.66534 (10)	−0.03723 (14)	0.0205 (3)
N3	0.34440 (6)	0.74619 (10)	0.04977 (13)	0.0205 (3)
C1	0.46166 (7)	0.50212 (12)	−0.22030 (17)	0.0228 (3)
H1A	0.4687	0.5799	−0.2432	0.027*
C2	0.49753 (8)	0.41733 (13)	−0.30194 (17)	0.0239 (3)
H2A	0.5287	0.4409	−0.3792	0.029*
C3	0.44347 (8)	0.27391 (13)	−0.16720 (19)	0.0310 (4)
H3A	0.4361	0.1955	−0.1492	0.037*
C4	0.40545 (8)	0.35211 (13)	−0.07883 (18)	0.0265 (3)
H4A	0.3738	0.3263	−0.0037	0.032*
C5	0.41511 (7)	0.46942 (12)	−0.10385 (15)	0.0182 (3)
C6	0.37626 (7)	0.55180 (12)	0.00140 (16)	0.0190 (3)
C7	0.33453 (7)	0.84479 (12)	−0.02067 (16)	0.0192 (3)
H7A	0.3528	0.8565	−0.1209	0.023*
C8	0.29549 (7)	0.93788 (12)	0.05350 (16)	0.0185 (3)
C9	0.29436 (7)	1.04692 (12)	−0.01554 (16)	0.0205 (3)
H9A	0.3198	1.0602	−0.1068	0.025*
C10	0.25541 (7)	1.13699 (12)	0.05066 (16)	0.0211 (3)
H10A	0.2556	1.2102	0.0044	0.025*
C11	0.21677 (7)	1.11759 (11)	0.18421 (16)	0.0182 (3)
C12	0.21699 (7)	1.00623 (11)	0.25633 (15)	0.0173 (3)
C13	0.25588 (7)	0.91782 (12)	0.18985 (16)	0.0186 (3)
H13A	0.2559	0.8445	0.2356	0.022*
C14	0.16762 (8)	0.88010 (12)	0.44760 (18)	0.0246 (3)
H14A	0.2148	0.8492	0.4839	0.030*
H14B	0.1466	0.8299	0.3641	0.030*
C15	0.11900 (7)	0.88528 (11)	0.58412 (17)	0.0197 (3)
C16	0.14817 (8)	0.90316 (12)	0.73981 (18)	0.0255 (3)
H16A	0.1983	0.9111	0.7585	0.031*
C17	0.10355 (9)	0.90916 (13)	0.86672 (18)	0.0312 (4)
H17A	0.1236	0.9215	0.9702	0.037*
C18	0.02901 (9)	0.89689 (13)	0.83993 (19)	0.0312 (4)
H18A	−0.0011	0.9007	0.9254	0.037*
C19	−0.00072 (8)	0.87894 (13)	0.6859 (2)	0.0318 (4)
H19A	−0.0508	0.8707	0.6677	0.038*
C20	0.04401 (8)	0.87320 (13)	0.55915 (18)	0.0260 (3)
H20A	0.0237	0.8611	0.4558	0.031*
C21	0.16494 (9)	1.30698 (12)	0.17427 (18)	0.0280 (3)
H21A	0.1321	1.3542	0.2310	0.042*
H21B	0.1449	1.2936	0.0671	0.042*
H21C	0.2109	1.3459	0.1703	0.042*
H1N2	0.4037 (9)	0.6892 (16)	−0.122 (2)	0.046 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0320 (5)	0.0276 (6)	0.0229 (5)	0.0005 (5)	0.0133 (5)	0.0027 (4)
O2	0.0252 (5)	0.0174 (5)	0.0203 (5)	0.0004 (4)	0.0108 (4)	0.0016 (4)
O3	0.0297 (5)	0.0164 (5)	0.0210 (5)	0.0043 (4)	0.0079 (4)	0.0011 (4)
N1	0.0284 (6)	0.0237 (6)	0.0258 (6)	0.0024 (5)	0.0045 (5)	−0.0026 (5)
N2	0.0244 (6)	0.0200 (6)	0.0179 (6)	0.0025 (5)	0.0094 (5)	−0.0010 (5)
N3	0.0211 (6)	0.0210 (6)	0.0201 (6)	0.0020 (5)	0.0076 (5)	−0.0033 (5)
C1	0.0271 (7)	0.0185 (7)	0.0236 (7)	0.0026 (6)	0.0083 (6)	0.0020 (6)
C2	0.0248 (7)	0.0265 (8)	0.0212 (7)	0.0042 (6)	0.0084 (6)	0.0012 (6)
C3	0.0362 (8)	0.0188 (7)	0.0390 (9)	−0.0011 (7)	0.0123 (7)	0.0000 (6)
C4	0.0271 (7)	0.0220 (7)	0.0315 (8)	0.0000 (6)	0.0113 (6)	0.0032 (6)
C5	0.0181 (6)	0.0211 (7)	0.0156 (6)	0.0020 (5)	0.0036 (5)	0.0004 (5)
C6	0.0187 (6)	0.0204 (7)	0.0183 (7)	0.0007 (5)	0.0038 (5)	0.0006 (5)
C7	0.0183 (6)	0.0223 (7)	0.0178 (6)	−0.0007 (5)	0.0062 (5)	−0.0009 (5)
C8	0.0171 (6)	0.0206 (7)	0.0180 (6)	−0.0010 (5)	0.0034 (5)	−0.0020 (5)
C9	0.0217 (7)	0.0224 (7)	0.0180 (7)	−0.0013 (6)	0.0060 (5)	0.0009 (5)
C10	0.0247 (7)	0.0182 (7)	0.0207 (7)	−0.0007 (6)	0.0034 (6)	0.0023 (5)
C11	0.0200 (6)	0.0174 (6)	0.0175 (6)	0.0003 (5)	0.0027 (5)	−0.0021 (5)
C12	0.0172 (6)	0.0187 (6)	0.0163 (6)	−0.0020 (5)	0.0049 (5)	−0.0011 (5)
C13	0.0193 (6)	0.0178 (6)	0.0190 (7)	−0.0001 (5)	0.0043 (5)	0.0011 (5)
C14	0.0287 (7)	0.0166 (7)	0.0301 (8)	0.0018 (6)	0.0139 (6)	0.0041 (6)
C15	0.0236 (7)	0.0142 (6)	0.0221 (7)	0.0016 (5)	0.0084 (6)	0.0016 (5)
C16	0.0274 (7)	0.0196 (7)	0.0294 (8)	−0.0022 (6)	−0.0005 (6)	0.0015 (6)
C17	0.0507 (10)	0.0242 (8)	0.0188 (7)	0.0000 (7)	0.0031 (7)	−0.0011 (6)
C18	0.0440 (9)	0.0239 (8)	0.0280 (8)	0.0008 (7)	0.0208 (7)	0.0000 (6)
C19	0.0238 (7)	0.0328 (9)	0.0401 (10)	−0.0015 (6)	0.0126 (7)	−0.0020 (7)
C20	0.0251 (7)	0.0315 (8)	0.0217 (7)	0.0011 (6)	0.0048 (6)	−0.0015 (6)
C21	0.0405 (9)	0.0181 (7)	0.0260 (8)	0.0074 (6)	0.0074 (7)	0.0032 (6)

Geometric parameters (Å, º) top

O1—C6	1.2249 (16)	C9—C10	1.3964 (19)
O2—C12	1.3628 (16)	C9—H9A	0.93
O2—C14	1.4423 (16)	C10—C11	1.3763 (19)
O3—C11	1.3633 (16)	C10—H10A	0.93
O3—C21	1.4391 (16)	C11—C12	1.4208 (18)
N1—C2	1.3354 (19)	C12—C13	1.3826 (18)
N1—C3	1.3414 (19)	C13—H13A	0.93
N2—C6	1.3560 (18)	C14—C15	1.492 (2)
N2—N3	1.3871 (16)	C14—H14A	0.97
N2—H1N2	0.885 (18)	C14—H14B	0.97
N3—C7	1.2902 (17)	C15—C20	1.390 (2)
C1—C2	1.3836 (19)	C15—C16	1.392 (2)
C1—C5	1.3861 (19)	C16—C17	1.380 (2)
C1—H1A	0.93	C16—H16A	0.93
C2—H2A	0.93	C17—C18	1.383 (2)
C3—C4	1.383 (2)	C17—H17A	0.93
C3—H3A	0.93	C18—C19	1.383 (2)
C4—C5	1.3849 (19)	C18—H18A	0.93
C4—H4A	0.93	C19—C20	1.380 (2)
C5—C6	1.5049 (19)	C19—H19A	0.93
C7—C8	1.4527 (19)	C20—H20A	0.93
C7—H7A	0.93	C21—H21A	0.96
C8—C9	1.3855 (19)	C21—H21B	0.96
C8—C13	1.4072 (18)	C21—H21C	0.96

C12—O2—C14	116.22 (10)	O3—C11—C12	114.78 (11)
C11—O3—C21	116.78 (10)	C10—C11—C12	120.17 (12)
C2—N1—C3	115.70 (13)	O2—C12—C13	125.30 (12)
C6—N2—N3	118.92 (12)	O2—C12—C11	115.49 (11)
C6—N2—H1N2	122.3 (12)	C13—C12—C11	119.18 (12)
N3—N2—H1N2	118.4 (12)	C12—C13—C8	120.56 (12)
C7—N3—N2	114.60 (11)	C12—C13—H13A	119.7
C2—C1—C5	119.03 (13)	C8—C13—H13A	119.7
C2—C1—H1A	120.5	O2—C14—C15	108.43 (11)
C5—C1—H1A	120.5	O2—C14—H14A	110.0
N1—C2—C1	124.35 (14)	C15—C14—H14A	110.0
N1—C2—H2A	117.8	O2—C14—H14B	110.0
C1—C2—H2A	117.8	C15—C14—H14B	110.0
N1—C3—C4	124.23 (14)	H14A—C14—H14B	108.4
N1—C3—H3A	117.9	C20—C15—C16	118.60 (13)
C4—C3—H3A	117.9	C20—C15—C14	121.09 (13)
C3—C4—C5	119.06 (14)	C16—C15—C14	120.30 (13)
C3—C4—H4A	120.5	C17—C16—C15	120.72 (14)
C5—C4—H4A	120.5	C17—C16—H16A	119.6
C4—C5—C1	117.58 (13)	C15—C16—H16A	119.6
C4—C5—C6	117.49 (12)	C16—C17—C18	119.99 (14)
C1—C5—C6	124.89 (13)	C16—C17—H17A	120.0
O1—C6—N2	123.42 (13)	C18—C17—H17A	120.0
O1—C6—C5	121.06 (13)	C19—C18—C17	119.91 (15)
N2—C6—C5	115.52 (12)	C19—C18—H18A	120.0
N3—C7—C8	121.29 (12)	C17—C18—H18A	120.0
N3—C7—H7A	119.4	C20—C19—C18	119.98 (14)
C8—C7—H7A	119.4	C20—C19—H19A	120.0
C9—C8—C13	119.41 (12)	C18—C19—H19A	120.0
C9—C8—C7	119.45 (12)	C19—C20—C15	120.79 (14)
C13—C8—C7	121.07 (12)	C19—C20—H20A	119.6
C8—C9—C10	120.56 (13)	C15—C20—H20A	119.6
C8—C9—H9A	119.7	O3—C21—H21A	109.5
C10—C9—H9A	119.7	O3—C21—H21B	109.5
C11—C10—C9	120.10 (13)	H21A—C21—H21B	109.5
C11—C10—H10A	120.0	O3—C21—H21C	109.5
C9—C10—H10A	120.0	H21A—C21—H21C	109.5
O3—C11—C10	125.04 (12)	H21B—C21—H21C	109.5

C6—N2—N3—C7	−160.87 (12)	C9—C10—C11—O3	−178.10 (12)
C3—N1—C2—C1	1.4 (2)	C9—C10—C11—C12	0.70 (19)
C5—C1—C2—N1	0.4 (2)	C14—O2—C12—C13	−5.78 (18)
C2—N1—C3—C4	−1.8 (2)	C14—O2—C12—C11	172.17 (11)
N1—C3—C4—C5	0.3 (2)	O3—C11—C12—O2	0.27 (16)
C3—C4—C5—C1	1.5 (2)	C10—C11—C12—O2	−178.65 (11)
C3—C4—C5—C6	−176.45 (12)	O3—C11—C12—C13	178.35 (11)
C2—C1—C5—C4	−1.84 (19)	C10—C11—C12—C13	−0.56 (19)
C2—C1—C5—C6	175.95 (12)	O2—C12—C13—C8	178.59 (12)
N3—N2—C6—O1	−2.77 (19)	C11—C12—C13—C8	0.71 (18)
N3—N2—C6—C5	177.17 (10)	C9—C8—C13—C12	−0.98 (19)
C4—C5—C6—O1	6.12 (19)	C7—C8—C13—C12	−177.89 (12)
C1—C5—C6—O1	−171.67 (13)	C12—O2—C14—C15	−178.00 (10)
C4—C5—C6—N2	−173.82 (12)	O2—C14—C15—C20	89.96 (15)
C1—C5—C6—N2	8.39 (18)	O2—C14—C15—C16	−89.64 (15)
N2—N3—C7—C8	178.85 (11)	C20—C15—C16—C17	−0.2 (2)
N3—C7—C8—C9	171.47 (12)	C14—C15—C16—C17	179.39 (13)
N3—C7—C8—C13	−11.63 (19)	C15—C16—C17—C18	0.3 (2)
C13—C8—C9—C10	1.11 (19)	C16—C17—C18—C19	−0.2 (2)
C7—C8—C9—C10	178.06 (12)	C17—C18—C19—C20	0.1 (2)
C8—C9—C10—C11	−0.98 (19)	C18—C19—C20—C15	0.0 (2)
C21—O3—C11—C10	7.50 (19)	C16—C15—C20—C19	0.1 (2)
C21—O3—C11—C12	−171.35 (11)	C14—C15—C20—C19	−179.52 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1ⁱ	0.88 (2)	2.54 (2)	3.3122 (17)	146 (1)
C9—H9A···O1ⁱⁱ	0.93	2.55	3.3524 (17)	144
C19—H19A···O3ⁱⁱⁱ	0.93	2.54	3.3960 (17)	153
C17—H17A···Cg1^iv	0.93	2.93	3.6694 (17)	137

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉N₃O₃
M_r	361.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	18.3930 (6), 11.5574 (4), 8.3508 (3)
β (°)	93.436 (2)
V (Å³)	1771.98 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.71 × 0.13 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.937, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	27863, 6434, 3841
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.145, 1.06
No. of reflections	6433
No. of parameters	249
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.28

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	0.88 (2)	2.54 (2)	3.3122 (17)	146 (1)
C9—H9A···O1ⁱⁱ	0.93	2.55	3.3524 (17)	144
C19—H19A···O3ⁱⁱⁱ	0.93	2.54	3.3960 (17)	153
C17—H17A···Cg1^iv	0.93	2.93	3.6694 (17)	137

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

Footnotes

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

§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. H-KF and W-SL thank USM for the Research University Golden Goose Grant No. 1001/PFIZIK/811012. W-SL also thanks the Malaysian government and USM for the award of the post of Assistant Research Officer under Research University Golden Goose Grant No. 1001/PFIZIK/811012. HSN is grateful for a USM fellowship for financial assistance.

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