2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone O-propyloxime

Özel Güven, Ö.; Erdoğan, T.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536809020844

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1517-o1518

doi:10.1107/S1600536809020844

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2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone O-propyloxime

Özden Özel Güven,^a Taner Erdoğan,^a Simon J. Coles ^b and Tuncer Hökelek ^c ^*

^aDepartment of Chemistry, Zonguldak Karaelmas University, 67100 Zonguldak, Turkey, ^bDepartment of Chemistry, Southampton University, SO17 1BJ Southampton, England, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 28 May 2009; accepted 2 June 2009; online 6 June 2009)

In the molecule of the title compound, C₁₆H₁₇N₃O₂, the planar benzimidazole ring system [maximum deviation = 0.013 (1) Å] is oriented at a dihedral angle of 75.32 (4)° with respect to the furan ring. An intramolecular C—H⋯O interaction results in the formation of a planar six-membered ring [maximum deviation = 0.019 (15) Å], which is oriented at a dihedral angle of 1.91 (3)° with respect to the adjacent furan ring. In the crystal structure, intermolecular C—H⋯N interactions link the molecules into centrosymmetric R₂²(18) dimers. In addition, the structure is stabilized by π–π contacts between the imidazole rings [centroid–centroid distance = 3.5307 (8) Å] and weak C—H⋯π interactions.

Related literature

Several compounds containing an oxime or an oxime ether function have been reported to exhibit antimicrobial activity, see: Baji et al. (1995 ); Bhandari et al. (2009 ); Emami et al. (2002 , 2004 ); Milanese et al. (2007 ); Polak (1982 ); Poretta et al. (1993 ); Ramalingan et al. (2006 ); Rosello et al. (2002 ). For related structures, see: Özel Güven et al. (2007a ,b ). For ring motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₇N₃O₂
M_r = 283.33
Monoclinic, P 2₁ /c
a = 8.4164 (2) Å
b = 18.2524 (3) Å
c = 10.2246 (2) Å
β = 111.354 (1)°
V = 1462.87 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 K
0.50 × 0.35 × 0.35 mm

Data collection

Bruker–Nonius Kappa CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.958, T_max = 0.960
19714 measured reflections
3344 independent reflections
2755 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.114
S = 1.14
3344 reflections
259 parameters
All H-atom parameters refined
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2	0.97 (2)	2.359 (16)	2.7930 (17)	106 (1)
C13—H13⋯N2ⁱ	0.96 (2)	2.360 (15)	3.2872 (17)	162 (1)
C14—H141⋯Cg1ⁱⁱ	0.99 (2)	2.968 (17)	3.8346 (16)	146 (1)
C16—H161⋯Cg2ⁱⁱ	0.99 (2)	2.685 (18)	3.5644 (16)	148 (1)
C16—H163⋯Cg3ⁱⁱ	1.00 (2)	2.643 (18)	3.5901 (15)	157 (1)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ . Cg1, Cg2 and Cg3 are the centroids of the C2–C7, N1/N2/C1/C2/C7 and O1/C10–C13 rings, respectively.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO nd COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020844/ci2817sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020844/ci2817Isup2.hkl

checkCIF report

Comment top

Oxiconazole (Polak, 1982) is a well known antifungal agent with a broad spectrum of activity, used for the treatment of skin mycoses. It is structurally characterized by an oxime ether group. Several compounds containing an oxime or an oxime ether function have been reported to exhibit antimicrobial activity (Poretta et al., 1993; Baji et al., 1995; Rosello et al., 2002; Emami et al., 2002; Emami et al., 2004; Ramalingan et al., 2006; Milanese et al., 2007; Bhandari et al., 2009). In our earlier studies, we reported the crystal structure of a benzimidazole substituted oxiconazole derivative (Özel Güven et al., 2007a). Now, we report herein the crystal structure of the title alkyl oxime ether.

In the molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges. The planar benzimidazole ring system is oriented with respect to the furan ring at a dihedral angle of 75.32 (4)°. Atoms O2, N3, C8, C9, C14 and C15 are 0.073 (1), 0.024 (1), -0.064 (1), -0.009 (1), 0.088 (1) and -0.082 (1) Å away from the furan ring plane, respectively, while atom C8 is at a distance of -0.007 (1) Å to the benzimidazole ring plane. So, they are coplanar with the adjacent rings. The N1—C1—N2 [114.29 (11)°], N2—C2—C7 [110.24 (11)°] and C2—C7—C6 [122.57 (11)°] bond angles are enlarged, while C5—C6—C7 [116.36 (11)°] and C2—C3—C4 [117.87 (11)°] bond angles are narrowed. An intramolecular C—H···O interaction (Table 1) results in the formation of a planar six-membered ring, (O2/N3/C9—C11/H11), which is oriented with respect to the adjacent furan ring at a dihedral angle of 1.91 (3)°. So, they are almost coplanar.

In the crystal structure, intermolecular C—H···N interactions (Table 1) link the molecules into centrosymmetric dimers through R₂²(18) ring motifs (Bernstein et al., 1995) (Fig. 2), in which they may be effective in the stabilization of the structure. The π···π contact between the benzimidazole rings [Cg2···Cg2ⁱ = 3.5307 (8) Å, where Cg1 is centroid of the N1/N2/C1/C2/C7 ring; symmetry code: (i) 2 - x, 1 -y, 2 - z] may further stabilize the structure. There also exist three weak C—H···π interactions (Table 1).

Related literature top

Several compounds containing an oxime or an oxime ether function have been reported to exhibit antimicrobial activity, see: Baji et al. (1995); Bhandari et al. (2009); Emami et al. (2002); Emami et al. (2004); Milanese et al. (2007); Polak (1982); Poretta et al. (1993); Ramalingan et al. (2006); Rosello et al. (2002). For related structures, see: Özel Güven et al. (2007a,b). For ring motifs, see: Bernstein et al. (1995). Cg1, Cg2 and Cg3 are the centroids of the C2–C7, N1/N2/C1/C2/C7 and O1/C10–C13 rings, respectively.

Experimental top

The title compound was synthesized by the reaction of 2-(1H-benzimidazol-1-yl)-1-(furan-2-yl)ethanone oxime obtained from 2-(1H-benzimidazol-1-yl)-1-(furan-2-yl)ethanone (Özel Güven et al., 2007b) with n-propyl bromide and NaH. To a solution of 2-(1H-benzimidazol-1-yl)-1-(furan-2-yl)ethanone oxime (350 mg, 1.451 mmol) in DMF (5 ml) was added NaH (58 mg, 1.451 mmol) in small fractions. Then, n-propyl bromide (178 mg, 1.451 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h and the excess of hydride was decomposed with a small amount of methyl alcohol. After evaporation to dryness under reduced pressure, the crude residue was suspended with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude product was purified by chromatography on a silica-gel column using chloroform and recrystallized from hexane-ethyl acetate (1:3) mixture to obtain pale-yellowish crystals (yield 150 mg, 37%).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a hydrogen bond.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone O-propyloxime top

Crystal data top

C₁₆H₁₇N₃O₂	F(000) = 600
M_r = 283.33	D_x = 1.286 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3395 reflections
a = 8.4164 (2) Å	θ = 2.9–27.5°
b = 18.2524 (3) Å	µ = 0.09 mm⁻¹
c = 10.2246 (2) Å	T = 120 K
β = 111.354 (1)°	Block, pale yellow
V = 1462.87 (5) Å³	0.50 × 0.35 × 0.35 mm
Z = 4

Data collection top

Bruker–Nonius Kappa CCD diffractometer	3344 independent reflections
Radiation source: fine-focus sealed tube	2755 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ϕ & ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −23→23
T_min = 0.958, T_max = 0.960	l = −13→13
19714 measured reflections

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)] = 0.043	All H-atom parameters refined
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0594P)² + 0.2758P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max = 0.001
3344 reflections	Δρ_max = 0.37 e Å⁻³
259 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.065 (5)

Crystal data top

C₁₆H₁₇N₃O₂	V = 1462.87 (5) Å³
M_r = 283.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4164 (2) Å	µ = 0.09 mm⁻¹
b = 18.2524 (3) Å	T = 120 K
c = 10.2246 (2) Å	0.50 × 0.35 × 0.35 mm
β = 111.354 (1)°

Data collection top

Bruker–Nonius Kappa CCD diffractometer	3344 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2755 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.960	R_int = 0.038
19714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.114	All H-atom parameters refined
S = 1.14	Δρ_max = 0.37 e Å⁻³
3344 reflections	Δρ_min = −0.36 e Å⁻³
259 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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	0.43354 (11)	0.47469 (5)	0.69234 (9)	0.0210 (2)
O2	0.62124 (10)	0.35487 (5)	0.44862 (9)	0.0215 (2)
N1	0.81649 (13)	0.45397 (6)	0.87655 (10)	0.0191 (2)
N2	0.81640 (14)	0.44200 (6)	1.09515 (11)	0.0234 (3)
N3	0.73483 (13)	0.39962 (6)	0.55091 (11)	0.0203 (2)
C1	0.75737 (16)	0.47823 (7)	0.97642 (13)	0.0226 (3)
H1	0.680 (2)	0.5192 (8)	0.9590 (16)	0.025 (4)*
C2	0.92279 (15)	0.38916 (7)	1.07227 (12)	0.0196 (3)
C3	1.01939 (16)	0.33471 (7)	1.16205 (13)	0.0229 (3)
H3	1.016 (2)	0.3284 (9)	1.2569 (17)	0.034 (4)*
C4	1.11688 (16)	0.28954 (7)	1.11299 (14)	0.0250 (3)
H4	1.185 (2)	0.2500 (9)	1.1699 (17)	0.035 (4)*
C5	1.11963 (16)	0.29780 (7)	0.97705 (14)	0.0249 (3)
H5	1.192 (2)	0.2655 (9)	0.9461 (16)	0.033 (4)*
C6	1.02292 (16)	0.35075 (7)	0.88540 (13)	0.0223 (3)
H6	1.0243 (19)	0.3573 (8)	0.7909 (16)	0.026 (4)*
C7	0.92492 (15)	0.39601 (6)	0.93600 (12)	0.0180 (3)
C8	0.77611 (17)	0.48381 (7)	0.73516 (13)	0.0209 (3)
H81	0.8843 (18)	0.4894 (8)	0.7176 (14)	0.018 (3)*
H82	0.7235 (19)	0.5324 (8)	0.7319 (15)	0.021 (4)*
C9	0.65977 (15)	0.43432 (6)	0.62241 (12)	0.0177 (3)
C10	0.48021 (15)	0.42984 (6)	0.60389 (12)	0.0176 (3)
C11	0.34138 (16)	0.39130 (7)	0.52080 (13)	0.0195 (3)
H11	0.3406 (18)	0.3571 (8)	0.4478 (15)	0.024 (4)*
C12	0.20149 (17)	0.41338 (7)	0.55880 (14)	0.0228 (3)
H12	0.081 (2)	0.3957 (8)	0.5195 (16)	0.027 (4)*
C13	0.26348 (17)	0.46348 (7)	0.66207 (13)	0.0233 (3)
H13	0.2152 (18)	0.4915 (8)	0.7179 (15)	0.021 (3)*
C14	0.71245 (17)	0.31673 (8)	0.37379 (15)	0.0269 (3)
H141	0.813 (2)	0.2925 (9)	0.4441 (17)	0.032 (4)*
H142	0.749 (2)	0.3531 (9)	0.3176 (17)	0.034 (4)*
C15	0.59066 (18)	0.26057 (8)	0.28123 (14)	0.0278 (3)
H151	0.650 (2)	0.2349 (10)	0.2257 (17)	0.040 (4)*
H152	0.493 (2)	0.2866 (9)	0.2113 (18)	0.040 (5)*
C16	0.52829 (18)	0.20602 (8)	0.36374 (15)	0.0287 (3)
H161	0.624 (2)	0.1794 (10)	0.4348 (19)	0.048 (5)*
H162	0.468 (2)	0.2317 (9)	0.4205 (16)	0.036 (4)*
H163	0.449 (2)	0.1687 (10)	0.3015 (19)	0.047 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0239 (5)	0.0207 (4)	0.0187 (4)	0.0014 (3)	0.0082 (4)	−0.0027 (3)
O2	0.0178 (4)	0.0252 (5)	0.0212 (4)	−0.0019 (3)	0.0069 (4)	−0.0078 (4)
N1	0.0206 (5)	0.0191 (5)	0.0163 (5)	−0.0009 (4)	0.0052 (4)	−0.0009 (4)
N2	0.0248 (6)	0.0258 (6)	0.0187 (5)	0.0015 (4)	0.0066 (4)	−0.0034 (4)
N3	0.0201 (5)	0.0212 (5)	0.0169 (5)	−0.0026 (4)	0.0036 (4)	−0.0013 (4)
C1	0.0234 (6)	0.0223 (6)	0.0213 (6)	0.0001 (5)	0.0070 (5)	−0.0053 (5)
C2	0.0179 (6)	0.0221 (6)	0.0173 (6)	−0.0037 (5)	0.0047 (5)	−0.0036 (5)
C3	0.0202 (6)	0.0275 (7)	0.0185 (6)	−0.0021 (5)	0.0041 (5)	0.0012 (5)
C4	0.0191 (6)	0.0252 (7)	0.0261 (7)	0.0017 (5)	0.0026 (5)	0.0025 (5)
C5	0.0187 (6)	0.0264 (7)	0.0293 (7)	0.0016 (5)	0.0083 (5)	−0.0036 (5)
C6	0.0200 (6)	0.0266 (6)	0.0212 (6)	−0.0027 (5)	0.0086 (5)	−0.0022 (5)
C7	0.0155 (5)	0.0188 (6)	0.0178 (6)	−0.0035 (4)	0.0036 (5)	−0.0016 (4)
C8	0.0238 (6)	0.0200 (6)	0.0165 (6)	−0.0042 (5)	0.0045 (5)	0.0009 (5)
C9	0.0206 (6)	0.0161 (6)	0.0150 (6)	−0.0009 (4)	0.0050 (5)	0.0029 (4)
C10	0.0229 (6)	0.0157 (5)	0.0146 (5)	0.0013 (4)	0.0074 (5)	0.0010 (4)
C11	0.0219 (6)	0.0185 (6)	0.0181 (6)	−0.0005 (5)	0.0073 (5)	−0.0001 (5)
C12	0.0216 (6)	0.0240 (6)	0.0237 (6)	0.0010 (5)	0.0093 (5)	0.0018 (5)
C13	0.0235 (6)	0.0257 (6)	0.0235 (6)	0.0045 (5)	0.0116 (5)	0.0020 (5)
C14	0.0212 (7)	0.0350 (7)	0.0277 (7)	0.0011 (6)	0.0128 (6)	−0.0079 (6)
C15	0.0249 (7)	0.0354 (8)	0.0232 (6)	0.0032 (6)	0.0087 (6)	−0.0095 (6)
C16	0.0258 (7)	0.0267 (7)	0.0305 (7)	0.0041 (6)	0.0067 (6)	−0.0070 (6)

Geometric parameters (Å, º) top

O1—C10	1.3787 (14)	C6—H6	0.978 (15)
O1—C13	1.3652 (16)	C8—H81	0.996 (14)
O2—N3	1.3952 (13)	C8—H82	0.987 (15)
O2—C14	1.4447 (15)	C9—C8	1.5105 (16)
N1—C1	1.3625 (16)	C9—C10	1.4553 (16)
N1—C7	1.3847 (15)	C11—C10	1.3635 (17)
N1—C8	1.4643 (15)	C11—C12	1.4257 (17)
N2—C1	1.3110 (17)	C11—H11	0.971 (15)
N2—C2	1.3927 (16)	C12—H12	0.999 (16)
N3—C9	1.2927 (16)	C13—C12	1.3499 (19)
C1—H1	0.963 (15)	C13—H13	0.959 (15)
C2—C3	1.3956 (18)	C14—H141	0.994 (16)
C2—C7	1.4055 (17)	C14—H142	0.999 (17)
C3—H3	0.987 (16)	C15—C14	1.5136 (19)
C4—C3	1.3800 (18)	C15—C16	1.517 (2)
C4—C5	1.4066 (19)	C15—H151	0.999 (17)
C4—H4	0.973 (17)	C15—H152	0.994 (18)
C5—H5	0.982 (16)	C16—H161	0.993 (19)
C6—C5	1.3854 (18)	C16—H162	1.015 (17)
C6—C7	1.3933 (17)	C16—H163	1.001 (19)

C13—O1—C10	106.73 (9)	N3—C9—C10	126.66 (11)
N3—O2—C14	109.14 (9)	N3—C9—C8	114.21 (11)
C1—N1—C7	106.35 (10)	C10—C9—C8	119.13 (10)
C1—N1—C8	127.02 (11)	C11—C10—O1	109.32 (10)
C7—N1—C8	126.62 (10)	C11—C10—C9	136.37 (11)
C1—N2—C2	104.12 (10)	O1—C10—C9	114.31 (10)
C9—N3—O2	111.61 (10)	C10—C11—C12	106.84 (11)
N1—C1—H1	121.3 (9)	C10—C11—H11	125.1 (9)
N2—C1—N1	114.29 (11)	C12—C11—H11	128.0 (9)
N2—C1—H1	124.4 (9)	C13—C12—C11	106.40 (11)
N2—C2—C3	129.71 (11)	C13—C12—H12	125.5 (9)
N2—C2—C7	110.24 (11)	C11—C12—H12	128.1 (9)
C3—C2—C7	120.05 (11)	C12—C13—O1	110.70 (11)
C4—C3—C2	117.87 (11)	C12—C13—H13	134.4 (9)
C4—C3—H3	121.4 (10)	O1—C13—H13	114.9 (9)
C2—C3—H3	120.7 (10)	O2—C14—C15	106.74 (10)
C3—C4—C5	121.40 (12)	O2—C14—H142	108.7 (9)
C3—C4—H4	121.7 (9)	C15—C14—H142	111.9 (9)
C5—C4—H4	116.9 (9)	O2—C14—H141	108.0 (9)
C6—C5—C4	121.75 (12)	C15—C14—H141	110.9 (9)
C6—C5—H5	118.9 (9)	H142—C14—H141	110.5 (13)
C4—C5—H5	119.4 (9)	C14—C15—C16	112.93 (11)
C5—C6—C7	116.36 (11)	C14—C15—H151	107.9 (10)
C5—C6—H6	122.6 (9)	C16—C15—H151	110.7 (10)
C7—C6—H6	121.1 (9)	C14—C15—H152	108.7 (10)
N1—C7—C6	132.42 (11)	C16—C15—H152	110.5 (10)
N1—C7—C2	105.01 (10)	H151—C15—H152	105.7 (13)
C6—C7—C2	122.57 (11)	C15—C16—H161	112.0 (10)
N1—C8—C9	112.58 (9)	C15—C16—H162	111.2 (9)
N1—C8—H81	108.5 (8)	H161—C16—H162	104.4 (13)
C9—C8—H81	107.8 (8)	C15—C16—H163	112.1 (10)
N1—C8—H82	108.0 (8)	H161—C16—H163	107.8 (15)
C9—C8—H82	110.7 (9)	H162—C16—H163	108.8 (14)
H81—C8—H82	109.2 (12)

C13—O1—C10—C11	−0.29 (13)	N2—C2—C7—N1	−0.36 (13)
C13—O1—C10—C9	−179.60 (10)	C3—C2—C7—N1	179.63 (11)
C10—O1—C13—C12	0.20 (13)	N2—C2—C7—C6	179.04 (11)
C14—O2—N3—C9	−179.10 (10)	C3—C2—C7—C6	−0.97 (18)
N3—O2—C14—C15	171.16 (10)	C5—C4—C3—C2	0.06 (19)
C7—N1—C1—N2	0.07 (15)	C3—C4—C5—C6	−1.0 (2)
C8—N1—C1—N2	−179.00 (11)	C7—C6—C5—C4	0.93 (18)
C1—N1—C7—C6	−179.14 (13)	C5—C6—C7—N1	179.26 (12)
C8—N1—C7—C6	−0.1 (2)	C5—C6—C7—C2	0.05 (18)
C1—N1—C7—C2	0.18 (13)	N3—C9—C8—N1	−106.07 (12)
C8—N1—C7—C2	179.25 (11)	C10—C9—C8—N1	73.98 (14)
C1—N1—C8—C9	−107.61 (14)	N3—C9—C10—C11	2.8 (2)
C7—N1—C8—C9	73.51 (15)	C8—C9—C10—C11	−177.25 (13)
C2—N2—C1—N1	−0.28 (14)	N3—C9—C10—O1	−178.13 (11)
C1—N2—C2—C3	−179.59 (13)	C8—C9—C10—O1	1.81 (15)
C1—N2—C2—C7	0.39 (13)	C12—C11—C10—O1	0.26 (13)
O2—N3—C9—C10	−0.07 (16)	C12—C11—C10—C9	179.35 (13)
O2—N3—C9—C8	179.98 (9)	C10—C11—C12—C13	−0.13 (14)
N2—C2—C3—C4	−179.13 (12)	O1—C13—C12—C11	−0.04 (14)
C7—C2—C3—C4	0.89 (18)	C16—C15—C14—O2	−59.43 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2	0.97 (2)	2.359 (16)	2.7930 (17)	106 (1)
C13—H13···N2ⁱ	0.96 (2)	2.360 (15)	3.2872 (17)	162 (1)
C14—H141···Cg1ⁱⁱ	0.99 (2)	2.968 (17)	3.8346 (16)	146 (1)
C16—H161···Cg2ⁱⁱ	0.99 (2)	2.685 (18)	3.5644 (16)	148 (1)
C16—H163···Cg3ⁱⁱ	1.00 (2)	2.643 (18)	3.5901 (15)	157 (1)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O₂
M_r	283.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	8.4164 (2), 18.2524 (3), 10.2246 (2)
β (°)	111.354 (1)
V (Å³)	1462.87 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.35 × 0.35

Data collection
Diffractometer	Bruker–Nonius Kappa CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.958, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	19714, 3344, 2755
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.114, 1.14
No. of reflections	3344
No. of parameters	259
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.36

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2	0.97 (2)	2.359 (16)	2.7930 (17)	106 (1)
C13—H13···N2ⁱ	0.96 (2)	2.360 (15)	3.2872 (17)	162 (1)
C14—H141···Cg1ⁱⁱ	0.99 (2)	2.968 (17)	3.8346 (16)	146 (1)
C16—H161···Cg2ⁱⁱ	0.99 (2)	2.685 (18)	3.5644 (16)	148 (1)
C16—H163···Cg3ⁱⁱ	1.00 (2)	2.643 (18)	3.5901 (15)	157 (1)

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

Acknowledgements

The authors acknowledge the Zonguldak Karaelmas University Research Fund (Project No. 2007/2–13-02–09).

References

Baji, H., Flammang, M., Kimny, T., Gasquez, F., Compagnon, P. L. & Delcourt, A. (1995). Eur. J. Med. Chem. 30, 617–626. CrossRef CAS Web of Science Google Scholar
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
Bhandari, K., Srinivas, N., Shiva Keshava, G. B. & Shukla, P. K. (2009). Eur. J. Med. Chem. 44, 437–447. Web of Science CrossRef PubMed CAS Google Scholar
Emami, S., Falahatti, M., Banifatemi, A., Moshiri, K. & Shafiee, A. (2002). Arch. Pharm. 335, 318–324. Web of Science CrossRef CAS Google Scholar
Emami, S., Falahatti, M., Banifatemi, A., Moshiri, K. & Shafiee, A. (2004). Bioorg. Med. Chem. 12, 5881–5889. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Milanese, L., Giacche, N., Schiaffella, F., Vecchiarelli, A., Macchiarulo, A. & Fringuelli, R. (2007). ChemMedChem, 2, 1208–1213. Web of Science CrossRef PubMed CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Özel Güven, Ö., Erdoğan, T., Çaylak, N. & Hökelek, T. (2007a). Acta Cryst. E63, o4090–o4091. Web of Science CSD CrossRef IUCr Journals Google Scholar
Özel Güven, Ö., Erdoğan, T., Göker, H. & Yıldız, S. (2007b). J. Heterocycl. Chem. 44, 731–734. Google Scholar
Polak, A. (1982). Arzneim. Forsch. Drug Res. 32, 17–24. CAS Google Scholar
Poretta, G. C., Fioravanti, R., Biava, M., Cirilli, R., Simonetti, N., Villa, A., Bello, U., Faccendini, P. & Tita, B. (1993). Eur. J. Med. Chem. 28, 749–760. CrossRef Web of Science Google Scholar
Ramalingan, C., Park, Y. T. & Kabilan, S. (2006). Eur. J. Med. Chem. 41, 683–696. Web of Science CrossRef PubMed CAS Google Scholar
Rosello, A., Bertini, S., Lapucci, A., Macchia, M., Martinelli, A., Rapposelli, S., Herreros, E. & Macchia, B. (2002). J. Med. Chem. 45, 4903–4912. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar