N′-[(1E,2E)-3,7-Dimethyl­octa-2,6-dien-1-yl­idene]pyridine-4-carbohydrazide

Bhat, M.A.; Abdel-Aziz, H.A.; Ghabbour, H.A.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536812009075

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1144-o1145

doi:10.1107/S1600536812009075

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N′-[(1E,2E)-3,7-Dimethylocta-2,6-dien-1-ylidene]pyridine-4-carbohydrazide

Mashooq A. Bhat,^a Hatem A. Abdel-Aziz,^a Hazem A. Ghabbour,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*‡

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 15 February 2012; accepted 29 February 2012; online 24 March 2012)

In the title compound, C₁₆H₂₁N₃O, the molecule adopts an E conformation about the central C=N double bond. The 2-methylpent-2-ene group is disordered over two sets of sites, with a refined occupancy ratio of 0.785 (8):0.215 (8). The dihedral angle between the essentially planar [the r.m.s. value for the major component is 0.021 (7) and its maximum deviation is 0.025 (4) Å; the r.m.s. value for the minor component is 0.03 (4) and its maximum deviation is 0.05 (3) Å] major and minor components of the 2-methylbut-2-ene group is 35.9 (13)°. In the crystal, C—H⋯O and N—H⋯O hydrogen bonds link the molecules, with the same O atom acting as the acceptor. This results in C¹₁(4) and C¹₁(5) [001] chains.

Related literature

For details and the biological activity of isoniazide, see: Janin (2007 ); Maccari et al. (2005 ); Slayden & Barry (2000 ); Hearn et al. (2009 ); Tripathi et al. (2011 ). For related structures, see: Naveenkumar et al. (2010); Jiang et al. (2009 ); Khan et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₂₁N₃O
M_r = 271.36
Monoclinic, P 2₁ /c
a = 17.5415 (8) Å
b = 12.0708 (6) Å
c = 7.8430 (4) Å
β = 101.854 (3)°
V = 1625.26 (14) Å³
Z = 4
Cu Kα radiation
μ = 0.56 mm⁻¹
T = 296 K
0.90 × 0.27 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.633, T_max = 0.912
16548 measured reflections
2978 independent reflections
2376 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.154
S = 1.03
2978 reflections
239 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O1ⁱ	0.873 (17)	2.052 (17)	2.9167 (18)	170.8 (16)
C4—H4A⋯O1ⁱ	0.93	2.53	3.251 (2)	135
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536812009075/lh5421sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009075/lh5421Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009075/lh5421Isup3.cml

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; Hearn et al., 2009; Tripathi et al., 2011). The crystal structures of (E)-N'- (2-Benzyloxybenzylidene)isonicotinohydrazide methanol solvate monohydrate (Naveenkumar et al., 2010), N'-(1-Phenylethylidene)isonicotino hydrazide (Jiang et al., 2009) and N'-(4-Bromophenylsulfonyl) isonicotinohydrazide (Khan et al., 2009) have been reported in the literature. Here, we present the crystal structure of the title compound, (I).

The asymmetric unit of the title compound is shown in Fig. 1. The molecule adopts an E configuration about the central C7═N2 double bond. The 2-methylpent-2-ene group is disordered over two sets of sites, with a refined occupancy ratio of 0.785 (8):0.215 (8). The dihedral angles between the major and minor components of the 2-methylbut-2-ene (C11–C15:C11A–C15A) group is 35.9 (13)°.

In the crystal, Fig. 2, the adjacent molecules are connected via bifurcated N—H···O and C—H···O hydrogen bonds (Table 1), generating R¹₂(7) ring motifs (Bernstein et al., 1995), resulting in supramolecular [001] chains.

Related literature top

For details and the biological activity of isoniazide, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000); Hearn et al. (2009); Tripathi et al. (2011). For related structures, see: Naveenkumar et al. (2010); Jiang et al. (2009); Khan et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by the reaction of citral, 3,7-dimethylocta- 2,6-dienal (0.15 g, 1 mmol) with isoniazid (0.14 g, 1 mmol) in ETOH/H₂O (3:1, v/v, 10 mL). After stirring for 3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue washed with cold ethyl alcohol and then with ethyl ether to afford the title compound. Colorless blocks of the latter compound suitable for X-ray structure determination were recrystallized from ETOH by the slow evaporation of the solvent at room temperature.

Structure description top

For details and the biological activity of isoniazide, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000); Hearn et al. (2009); Tripathi et al. (2011). For related structures, see: Naveenkumar et al. (2010); Jiang et al. (2009); Khan et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. Open bonds represent disordered components.
	Fig. 2. The crystal packing of the title compound (I). Hydrogen bonds are shown as dashed lines. The disorder is not shown.

N'-[(1E,2E)-3,7-Dimethylocta-2,6-dien-1-ylidene]pyridine- 4-carbohydrazide top

Crystal data top

C₁₆H₂₁N₃O	F(000) = 584
M_r = 271.36	D_x = 1.109 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1053 reflections
a = 17.5415 (8) Å	θ = 11.3–69.5°
b = 12.0708 (6) Å	µ = 0.56 mm⁻¹
c = 7.8430 (4) Å	T = 296 K
β = 101.854 (3)°	Block, colourless
V = 1625.26 (14) Å³	0.90 × 0.27 × 0.17 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2978 independent reflections
Radiation source: fine-focus sealed tube	2376 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 69.7°, θ_min = 5.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→21
T_min = 0.633, T_max = 0.912	k = −14→14
16548 measured reflections	l = −9→7

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0826P)² + 0.2272P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2978 reflections	Δρ_max = 0.13 e Å⁻³
239 parameters	Δρ_min = −0.14 e Å⁻³
12 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (6)

Crystal data top

C₁₆H₂₁N₃O	V = 1625.26 (14) Å³
M_r = 271.36	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 17.5415 (8) Å	µ = 0.56 mm⁻¹
b = 12.0708 (6) Å	T = 296 K
c = 7.8430 (4) Å	0.90 × 0.27 × 0.17 mm
β = 101.854 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2978 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2376 reflections with I > 2σ(I)
T_min = 0.633, T_max = 0.912	R_int = 0.027
16548 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	12 restraints
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.13 e Å⁻³
2978 reflections	Δρ_min = −0.14 e Å⁻³
239 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	Occ. (<1)
O1	0.30512 (6)	0.61845 (10)	0.31148 (14)	0.0640 (3)
N1	0.06078 (9)	0.62725 (17)	0.5444 (3)	0.0897 (5)
N2	0.40983 (7)	0.76093 (12)	0.49025 (19)	0.0656 (4)
N3	0.33659 (7)	0.74425 (12)	0.52777 (18)	0.0602 (4)
C1	0.09771 (12)	0.54801 (19)	0.4767 (3)	0.0905 (7)
H1A	0.0724	0.4805	0.4511	0.109*
C2	0.17110 (10)	0.55920 (16)	0.4418 (3)	0.0746 (5)
H2A	0.1942	0.5007	0.3941	0.090*
C3	0.20985 (8)	0.65855 (13)	0.47852 (19)	0.0558 (4)
C4	0.17217 (9)	0.74139 (15)	0.5489 (2)	0.0686 (5)
H4A	0.1959	0.8099	0.5756	0.082*
C5	0.09864 (10)	0.72159 (19)	0.5792 (3)	0.0822 (6)
H5A	0.0742	0.7785	0.6274	0.099*
C6	0.28809 (8)	0.67137 (13)	0.43211 (19)	0.0534 (4)
C7	0.45447 (9)	0.82229 (15)	0.6011 (2)	0.0645 (4)
H7A	0.4366	0.8509	0.6957	0.077*
C8	0.53221 (10)	0.84735 (17)	0.5801 (3)	0.0746 (5)
H8A	0.5485	0.8169	0.4846	0.089*
C9	0.58251 (11)	0.91090 (18)	0.6876 (3)	0.0837 (6)
C10	0.66541 (16)	0.9344 (4)	0.6696 (6)	0.0871 (10)	0.785 (8)
H10A	0.6713	1.0139	0.6600	0.105*	0.785 (8)
H10B	0.7002	0.9109	0.7762	0.105*	0.785 (8)
C11	0.69190 (18)	0.8806 (3)	0.5187 (5)	0.0900 (11)	0.785 (8)
H11A	0.6929	0.8008	0.5341	0.108*	0.785 (8)
H11B	0.6550	0.8975	0.4118	0.108*	0.785 (8)
C12	0.77113 (18)	0.9196 (3)	0.5033 (6)	0.0828 (10)	0.785 (8)
H12A	0.7710	0.9863	0.4439	0.099*	0.785 (8)
C13	0.8396 (4)	0.8782 (5)	0.5571 (15)	0.0811 (19)	0.785 (8)
C14	0.9134 (3)	0.9352 (6)	0.5393 (11)	0.1003 (15)	0.785 (8)
H14A	0.9011	1.0045	0.4798	0.150*	0.785 (8)
H14B	0.9416	0.8891	0.4739	0.150*	0.785 (8)
H14C	0.9448	0.9486	0.6529	0.150*	0.785 (8)
C15	0.8582 (5)	0.7702 (6)	0.6537 (11)	0.162 (3)	0.785 (8)
H15A	0.8121	0.7420	0.6863	0.242*	0.785 (8)
H15B	0.8977	0.7823	0.7564	0.242*	0.785 (8)
H15C	0.8766	0.7175	0.5797	0.242*	0.785 (8)
C10A	0.6475 (6)	0.9475 (14)	0.5992 (19)	0.0871 (10)	0.215 (8)
H10C	0.6314	0.9371	0.4743	0.105*	0.215 (8)
H10D	0.6577	1.0258	0.6210	0.105*	0.215 (8)
C11A	0.7184 (8)	0.8848 (17)	0.663 (4)	0.169 (13)	0.215 (8)
H11C	0.7112	0.8104	0.6156	0.203*	0.215 (8)
H11D	0.7257	0.8787	0.7887	0.203*	0.215 (8)
C12A	0.7911 (7)	0.9321 (12)	0.620 (4)	0.123 (7)	0.215 (8)
H12B	0.7971	1.0081	0.6089	0.148*	0.215 (8)
C13A	0.8464 (13)	0.8625 (17)	0.599 (5)	0.080 (8)	0.215 (8)
C14A	0.9212 (14)	0.901 (3)	0.562 (6)	0.170 (16)	0.215 (8)
H14D	0.9258	0.9793	0.5797	0.255*	0.215 (8)
H14E	0.9232	0.8837	0.4434	0.255*	0.215 (8)
H14F	0.9633	0.8641	0.6388	0.255*	0.215 (8)
C15A	0.8294 (13)	0.7391 (13)	0.588 (4)	0.137 (8)	0.215 (8)
H15D	0.7743	0.7273	0.5742	0.206*	0.215 (8)
H15E	0.8562	0.7036	0.6925	0.206*	0.215 (8)
H15F	0.8468	0.7084	0.4895	0.206*	0.215 (8)
C16	0.56438 (16)	0.9641 (3)	0.8453 (4)	0.1287 (12)
H16A	0.5169	0.9337	0.8683	0.193*
H16B	0.5584	1.0424	0.8265	0.193*
H16C	0.6061	0.9505	0.9432	0.193*
H1N3	0.3250 (10)	0.7786 (15)	0.617 (2)	0.063 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0566 (6)	0.0690 (7)	0.0683 (7)	−0.0046 (5)	0.0170 (5)	−0.0065 (5)
N1	0.0508 (8)	0.1053 (13)	0.1165 (14)	−0.0154 (8)	0.0259 (8)	−0.0068 (10)
N2	0.0505 (7)	0.0773 (9)	0.0744 (8)	−0.0136 (6)	0.0255 (6)	−0.0094 (7)
N3	0.0465 (7)	0.0721 (9)	0.0658 (8)	−0.0116 (6)	0.0201 (6)	−0.0093 (6)
C1	0.0625 (10)	0.0804 (13)	0.1331 (18)	−0.0218 (10)	0.0307 (11)	−0.0046 (12)
C2	0.0580 (9)	0.0658 (10)	0.1026 (13)	−0.0102 (8)	0.0223 (9)	−0.0010 (9)
C3	0.0449 (7)	0.0622 (9)	0.0593 (8)	−0.0041 (6)	0.0088 (6)	0.0055 (7)
C4	0.0483 (8)	0.0737 (11)	0.0836 (11)	−0.0076 (7)	0.0132 (7)	−0.0115 (8)
C5	0.0489 (9)	0.0978 (14)	0.1012 (14)	−0.0048 (9)	0.0183 (9)	−0.0194 (11)
C6	0.0462 (7)	0.0559 (8)	0.0584 (8)	−0.0027 (6)	0.0113 (6)	0.0051 (6)
C7	0.0512 (8)	0.0720 (10)	0.0741 (10)	−0.0121 (7)	0.0217 (7)	−0.0097 (8)
C8	0.0554 (9)	0.0845 (12)	0.0895 (12)	−0.0165 (8)	0.0281 (8)	−0.0174 (9)
C9	0.0561 (10)	0.0823 (13)	0.1158 (15)	−0.0172 (9)	0.0251 (10)	−0.0202 (11)
C10	0.0477 (14)	0.0936 (18)	0.117 (3)	−0.0193 (15)	0.0097 (16)	−0.015 (2)
C11	0.0575 (16)	0.111 (2)	0.107 (2)	−0.0183 (15)	0.0294 (15)	−0.0033 (18)
C12	0.0540 (15)	0.0843 (19)	0.113 (2)	−0.0069 (13)	0.0249 (15)	0.0191 (18)
C13	0.078 (3)	0.077 (3)	0.093 (4)	0.007 (2)	0.026 (2)	0.018 (3)
C14	0.0549 (18)	0.110 (4)	0.140 (3)	0.004 (2)	0.030 (2)	0.001 (3)
C15	0.162 (6)	0.127 (5)	0.209 (7)	0.022 (4)	0.068 (5)	0.075 (5)
C10A	0.0477 (14)	0.0936 (18)	0.117 (3)	−0.0193 (15)	0.0097 (16)	−0.015 (2)
C11A	0.081 (9)	0.146 (15)	0.29 (3)	0.031 (9)	0.064 (14)	0.12 (2)
C12A	0.064 (7)	0.086 (8)	0.22 (2)	−0.013 (6)	0.039 (11)	0.026 (12)
C13A	0.072 (8)	0.069 (9)	0.11 (2)	0.023 (6)	0.037 (10)	0.034 (8)
C14A	0.095 (14)	0.12 (2)	0.28 (4)	0.012 (12)	0.001 (16)	−0.03 (2)
C15A	0.121 (14)	0.070 (9)	0.20 (2)	0.029 (9)	−0.008 (12)	−0.009 (10)
C16	0.0951 (17)	0.160 (3)	0.137 (2)	−0.0471 (18)	0.0378 (15)	−0.071 (2)

Geometric parameters (Å, º) top

O1—C6	1.2283 (18)	C12—C13	1.290 (7)
N1—C5	1.318 (3)	C12—H12A	0.9300
N1—C1	1.326 (3)	C13—C14	1.497 (6)
N2—C7	1.280 (2)	C13—C15	1.510 (7)
N2—N3	1.3903 (17)	C14—H14A	0.9600
N3—C6	1.341 (2)	C14—H14B	0.9600
N3—H1N3	0.873 (18)	C14—H14C	0.9600
C1—C2	1.377 (2)	C15—H15A	0.9600
C1—H1A	0.9300	C15—H15B	0.9600
C2—C3	1.379 (2)	C15—H15C	0.9600
C2—H2A	0.9300	C10A—C11A	1.454 (14)
C3—C4	1.375 (2)	C10A—H10C	0.9700
C3—C6	1.4985 (18)	C10A—H10D	0.9700
C4—C5	1.380 (2)	C11A—C12A	1.497 (13)
C4—H4A	0.9300	C11A—H11C	0.9700
C5—H5A	0.9300	C11A—H11D	0.9700
C7—C8	1.439 (2)	C12A—C13A	1.320 (16)
C7—H7A	0.9300	C12A—H12B	0.9300
C8—C9	1.331 (3)	C13A—C14A	1.474 (16)
C8—H8A	0.9300	C13A—C15A	1.518 (17)
C9—C16	1.485 (3)	C14A—H14D	0.9600
C9—C10	1.516 (2)	C14A—H14E	0.9600
C9—C10A	1.517 (3)	C14A—H14F	0.9600
C10—C11	1.505 (4)	C15A—H15D	0.9600
C10—H10A	0.9700	C15A—H15E	0.9600
C10—H10B	0.9700	C15A—H15F	0.9600
C11—C12	1.496 (4)	C16—H16A	0.9600
C11—H11A	0.9700	C16—H16B	0.9600
C11—H11B	0.9700	C16—H16C	0.9600

C5—N1—C1	116.07 (15)	C12—C13—C15	126.1 (5)
C7—N2—N3	113.78 (13)	C14—C13—C15	110.0 (6)
C6—N3—N2	118.96 (13)	C13—C14—H14A	109.5
C6—N3—H1N3	122.3 (12)	C13—C14—H14B	109.5
N2—N3—H1N3	118.6 (12)	H14A—C14—H14B	109.5
N1—C1—C2	124.24 (18)	C13—C14—H14C	109.5
N1—C1—H1A	117.9	H14A—C14—H14C	109.5
C2—C1—H1A	117.9	H14B—C14—H14C	109.5
C1—C2—C3	118.98 (18)	C13—C15—H15A	109.5
C1—C2—H2A	120.5	C13—C15—H15B	109.5
C3—C2—H2A	120.5	H15A—C15—H15B	109.5
C4—C3—C2	117.33 (14)	C13—C15—H15C	109.5
C4—C3—C6	124.20 (14)	H15A—C15—H15C	109.5
C2—C3—C6	118.40 (15)	H15B—C15—H15C	109.5
C3—C4—C5	119.13 (17)	C11A—C10A—C9	111.1 (10)
C3—C4—H4A	120.4	C11A—C10A—H10C	109.4
C5—C4—H4A	120.4	C9—C10A—H10C	109.4
N1—C5—C4	124.25 (18)	C11A—C10A—H10D	109.4
N1—C5—H5A	117.9	C9—C10A—H10D	109.4
C4—C5—H5A	117.9	H10C—C10A—H10D	108.0
O1—C6—N3	123.05 (13)	C10A—C11A—C12A	115.6 (10)
O1—C6—C3	120.88 (13)	C10A—C11A—H11C	108.4
N3—C6—C3	116.06 (13)	C12A—C11A—H11C	108.4
N2—C7—C8	120.42 (15)	C10A—C11A—H11D	108.4
N2—C7—H7A	119.8	C12A—C11A—H11D	108.4
C8—C7—H7A	119.8	H11C—C11A—H11D	107.5
C9—C8—C7	124.73 (17)	C13A—C12A—C11A	117.9 (14)
C9—C8—H8A	117.6	C13A—C12A—H12B	121.0
C7—C8—H8A	117.6	C11A—C12A—H12B	121.0
C8—C9—C16	123.28 (17)	C12A—C13A—C14A	122.2 (17)
C8—C9—C10	124.9 (2)	C12A—C13A—C15A	119.4 (16)
C16—C9—C10	111.7 (2)	C14A—C13A—C15A	118.0 (18)
C8—C9—C10A	110.0 (7)	C13A—C14A—H14D	109.5
C16—C9—C10A	124.4 (7)	C13A—C14A—H14E	109.5
C10—C9—C10A	22.7 (5)	H14D—C14A—H14E	109.5
C11—C10—C9	116.7 (3)	C13A—C14A—H14F	109.5
C11—C10—H10A	108.1	H14D—C14A—H14F	109.5
C9—C10—H10A	108.1	H14E—C14A—H14F	109.5
C11—C10—H10B	108.1	C13A—C15A—H15D	109.5
C9—C10—H10B	108.1	C13A—C15A—H15E	109.5
H10A—C10—H10B	107.3	H15D—C15A—H15E	109.5
C12—C11—C10	111.7 (3)	C13A—C15A—H15F	109.5
C12—C11—H11A	109.3	H15D—C15A—H15F	109.5
C10—C11—H11A	109.3	H15E—C15A—H15F	109.5
C12—C11—H11B	109.3	C9—C16—H16A	109.5
C10—C11—H11B	109.3	C9—C16—H16B	109.5
H11A—C11—H11B	107.9	H16A—C16—H16B	109.5
C13—C12—C11	132.1 (4)	C9—C16—H16C	109.5
C13—C12—H12A	113.9	H16A—C16—H16C	109.5
C11—C12—H12A	113.9	H16B—C16—H16C	109.5
C12—C13—C14	123.8 (6)

C7—N2—N3—C6	−172.49 (15)	C7—C8—C9—C16	0.4 (4)
C5—N1—C1—C2	−0.2 (4)	C7—C8—C9—C10	177.8 (3)
N1—C1—C2—C3	0.0 (4)	C7—C8—C9—C10A	−162.8 (6)
C1—C2—C3—C4	0.0 (3)	C8—C9—C10—C11	−0.3 (6)
C1—C2—C3—C6	−177.16 (18)	C16—C9—C10—C11	177.4 (4)
C2—C3—C4—C5	0.1 (3)	C10A—C9—C10—C11	−54.2 (19)
C6—C3—C4—C5	177.14 (16)	C9—C10—C11—C12	173.7 (3)
C1—N1—C5—C4	0.3 (3)	C10—C11—C12—C13	96.6 (9)
C3—C4—C5—N1	−0.3 (3)	C11—C12—C13—C14	−175.3 (6)
N2—N3—C6—O1	−0.3 (2)	C11—C12—C13—C15	1.4 (15)
N2—N3—C6—C3	−179.34 (13)	C8—C9—C10A—C11A	−103 (2)
C4—C3—C6—O1	−149.52 (17)	C16—C9—C10A—C11A	94 (2)
C2—C3—C6—O1	27.5 (2)	C10—C9—C10A—C11A	31.7 (18)
C4—C3—C6—N3	29.5 (2)	C9—C10A—C11A—C12A	−165.1 (17)
C2—C3—C6—N3	−153.47 (16)	C10A—C11A—C12A—C13A	−149 (3)
N3—N2—C7—C8	−179.95 (16)	C11A—C12A—C13A—C14A	−178 (3)
N2—C7—C8—C9	179.4 (2)	C11A—C12A—C13A—C15A	10 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O1ⁱ	0.873 (17)	2.052 (17)	2.9167 (18)	170.8 (16)
C4—H4A···O1ⁱ	0.93	2.53	3.251 (2)	135

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₁N₃O
M_r	271.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	17.5415 (8), 12.0708 (6), 7.8430 (4)
β (°)	101.854 (3)
V (Å³)	1625.26 (14)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.90 × 0.27 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.633, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	16548, 2978, 2376
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.154, 1.03
No. of reflections	2978
No. of parameters	239
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

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
N3—H1N3···O1ⁱ	0.873 (17)	2.052 (17)	2.9167 (18)	170.8 (16)
C4—H4A···O1ⁱ	0.9300	2.5300	3.251 (2)	135.00

Symmetry code: (i) x, −y+3/2, z+1/2.

Footnotes

‡College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

MAB, HAA and HAG thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. MH and HFK thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hearn, M. J., Cynamon, M. H., Chen, M. F., Coppinsa, R., Davis, J., Joo-On Kang, H., Noble, A., Tu-Sekine, B., Terrot, M. S., Trombino, D., Thai, M., Webster, E. R. & Wilson. R. (2009). Eur. J. Med. Chem. 44, 4169–4178. Google Scholar
Janin, Y. L. (2007). Bioorg. Med. Chem. 15, 2479–2513. Web of Science CrossRef PubMed CAS Google Scholar
Jiang, J., Chen, J., Yang, J. & Jian, F.-F. (2009). Acta Cryst. E65, o3125. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khan, I. U., Ashfaq, M., Arshad, M. N., Ahmad, H. & Mustafa, G. (2009). Acta Cryst. E65, o1991. Web of Science CSD CrossRef IUCr Journals 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., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o1337–o1338. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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
Tripathi, L., Singh, R. & Stables, J. P. (2011). Eur. J. Med. Chem. 46, 509–518. Web of Science CrossRef CAS PubMed Google Scholar