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

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

doi:10.1107/S1600536809022302

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1604-o1605

doi:10.1107/S1600536809022302

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

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

(Received 8 June 2009; accepted 11 June 2009; online 17 June 2009)

In the molecule of the title compound, C₁₆H₁₇N₃O₂, the planar benzimidazole ring system [maximum deviation = 0.015 (2) Å] is oriented at a dihedral angle of 72.17 (4)° with respect to the furan ring. An intramolecular C—H⋯O interaction results in the formation of a six-membered ring having an envelope conformation. In the crystal structure, intermolecular C—H⋯N interactions link the molecules into centrosymmetric R₂²(18) dimers.

Related literature

For general background to oximes and oxime ethers, including their biological 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 , 2009 ). For ring-motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₇N₃O₂
M_r = 283.33
Monoclinic, P 2₁ /c
a = 8.4290 (2) Å
b = 17.7606 (3) Å
c = 10.6017 (2) Å
β = 111.882 (1)°
V = 1472.77 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.966, T_max = 0.979
20597 measured reflections
3356 independent reflections
2803 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.111
S = 1.12
3356 reflections
259 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2	0.98 (2)	2.32 (2)	2.772 (2)	107 (1)
C13—H13⋯N2ⁱ	0.96 (2)	2.37 (2)	3.286 (2)	159 (1)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and 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/S1600536809022302/im2123sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022302/im2123Isup2.hkl

checkCIF report

Comment top

Oximes and oxime ethers show very important antifungal and antibacterial activities. Oxiconazole is a well established drug for treatment of many mycotic infections, having an oxime group (Polak, 1982). 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 X-ray structures of benzimidazole substituted oxiconazole derivatives (Özel Güven et al., 2007a; 2007b; 2009). 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 [with a maximum deviation of 0.015 (2) Å for atom C5] is oriented with respect to the furan ring at a dihedral angle of 72.17 (4)°. Atoms C8 and C9 are -0.037 (1) and 0.008 (1) Å away from the furan ring plane, respectively, while atom C8 is at a distance of -0.008 (1) Å to the benzimidazole ring plane. So, they are coplanar with the adjacent rings. The N1—C1—N2 [114.1 (1)°], N2—C2—C7 [110.2 (1)°], C2—C7—C6 [122.8 (1)°], C3—C4—C5 [121.7 (1)°] and C4—C5—C6 [121.8 (1)°] bond angles are enlarged, while C5—C6—C7 [116.2 (1)°] and C2—C3—C4 [117.5 (1)°] bond angles are narrowed. An Intramolecular C—H···O interaction (Table 1) results in the formation of a six-membered ring, (O2/N3/C9—C11/H11), having envelope conformation with atom H11 displaced by -0.126 (15) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular C—H···N interactions (Table 1) link the molecules into centrosymmetric dimers exhibiting R₂²(18) ring motifs (Bernstein et al., 1995) (Fig. 2).

Related literature top

For general backgroud to oximes and oxime ethers, including their biological 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, 2009). For ring-motifs, see: Bernstein et al. (1995).

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 iso-propyl bromide and NaH. To a solution of 2-(1H-benzimidazol-1-yl)-1-(furan-2-yl)ethanone oxime (400 mg, 1.658 mmol) in DMF (5 ml) was added NaH (66 mg, 1.658 mmol) in small fractions. Then, iso-propyl bromide (204 mg, 1.658 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 methanol. 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 residue was purified by chromatography on a silica-gel column using chloroform and recrystallized from ethyl acetate to obtain yellow crystals (yield; 126 mg, 27%).

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 molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bond is shown as dashed line.
	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-isopropyloxime top

Crystal data top

C₁₆H₁₇N₃O₂	F(000) = 600
M_r = 283.33	D_x = 1.278 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3444 reflections
a = 8.4290 (2) Å	θ = 2.9–27.5°
b = 17.7606 (3) Å	µ = 0.09 mm⁻¹
c = 10.6017 (2) Å	T = 120 K
β = 111.882 (1)°	Plate, yellow
V = 1472.77 (5) Å³	0.40 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker–Nonius KappaCCD diffractometer	3356 independent reflections
Radiation source: fine-focus sealed tube	2803 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −23→23
T_min = 0.966, T_max = 0.979	l = −13→12
20597 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)] = 0.042	All H-atom parameters refined
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0577P)² + 0.2982P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
3356 reflections	Δρ_max = 0.27 e Å⁻³
259 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.091 (6)

Crystal data top

C₁₆H₁₇N₃O₂	V = 1472.77 (5) Å³
M_r = 283.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4290 (2) Å	µ = 0.09 mm⁻¹
b = 17.7606 (3) Å	T = 120 K
c = 10.6017 (2) Å	0.40 × 0.20 × 0.20 mm
β = 111.882 (1)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	3356 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2803 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.979	R_int = 0.035
20597 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.111	All H-atom parameters refined
S = 1.12	Δρ_max = 0.27 e Å⁻³
3356 reflections	Δρ_min = −0.28 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	0.58682 (11)	0.47550 (5)	0.80555 (8)	0.0252 (2)
O2	0.41827 (11)	0.33276 (5)	1.02341 (8)	0.0247 (2)
N1	0.19899 (13)	0.45752 (5)	0.64047 (9)	0.0205 (2)
N2	0.18669 (14)	0.44880 (6)	0.42568 (10)	0.0278 (3)
N3	0.30106 (13)	0.38505 (6)	0.94150 (10)	0.0226 (2)
C1	0.25496 (17)	0.48323 (7)	0.54285 (12)	0.0244 (3)
H1	0.3367 (18)	0.5250 (8)	0.5619 (14)	0.025 (3)*
C2	0.07716 (15)	0.39595 (7)	0.44673 (12)	0.0241 (3)
C3	−0.03026 (17)	0.34334 (8)	0.35695 (13)	0.0318 (3)
H3	−0.032 (2)	0.3408 (9)	0.2646 (17)	0.038 (4)*
C4	−0.12897 (19)	0.29830 (9)	0.40499 (15)	0.0386 (4)
H4	−0.203 (2)	0.2612 (11)	0.3450 (18)	0.051 (5)*
C5	−0.12247 (18)	0.30444 (8)	0.53863 (15)	0.0360 (3)
H5	−0.196 (2)	0.2724 (10)	0.5696 (17)	0.045 (5)*
C6	−0.01575 (16)	0.35542 (7)	0.62975 (14)	0.0282 (3)
H6	−0.0111 (19)	0.3597 (8)	0.7232 (16)	0.031 (4)*
C7	0.08317 (14)	0.40074 (6)	0.58065 (11)	0.0212 (3)
C8	0.25028 (16)	0.48361 (7)	0.78092 (12)	0.0222 (3)
H81	0.3035 (17)	0.5328 (8)	0.7868 (13)	0.022 (3)*
H82	0.1471 (19)	0.4885 (8)	0.8028 (14)	0.026 (4)*
C9	0.37140 (15)	0.42870 (6)	0.87967 (11)	0.0197 (3)
C10	0.54860 (15)	0.42703 (6)	0.89174 (11)	0.0198 (3)
C11	0.69233 (16)	0.38863 (7)	0.96787 (12)	0.0236 (3)
H11	0.6964 (19)	0.3507 (9)	1.0364 (15)	0.030 (4)*
C12	0.82605 (17)	0.41455 (7)	0.92724 (13)	0.0289 (3)
H12	0.941 (2)	0.3979 (9)	0.9589 (17)	0.040 (4)*
C13	0.75635 (17)	0.46619 (8)	0.82951 (13)	0.0296 (3)
H13	0.799 (2)	0.4959 (9)	0.7728 (16)	0.037 (4)*
C14	0.33484 (16)	0.28212 (7)	1.08724 (13)	0.0265 (3)
H14	0.219 (2)	0.2716 (9)	1.0207 (15)	0.031 (4)*
C15	0.3264 (3)	0.31843 (10)	1.21285 (18)	0.0463 (4)
H151	0.446 (3)	0.3321 (12)	1.281 (2)	0.061 (6)*
H152	0.254 (3)	0.3634 (12)	1.189 (2)	0.060 (6)*
H153	0.272 (3)	0.2848 (11)	1.2585 (19)	0.060 (5)*
C16	0.44161 (18)	0.21125 (8)	1.11657 (14)	0.0316 (3)
H161	0.446 (2)	0.1863 (10)	1.0273 (18)	0.048 (5)*
H162	0.398 (2)	0.1768 (10)	1.1676 (18)	0.048 (5)*
H163	0.559 (2)	0.2239 (9)	1.1768 (17)	0.040 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0290 (5)	0.0255 (4)	0.0222 (4)	−0.0023 (3)	0.0109 (4)	0.0052 (3)
O2	0.0236 (5)	0.0258 (4)	0.0235 (4)	−0.0009 (3)	0.0075 (3)	0.0090 (3)
N1	0.0244 (5)	0.0197 (5)	0.0171 (5)	0.0029 (4)	0.0074 (4)	0.0016 (4)
N2	0.0345 (6)	0.0279 (5)	0.0204 (5)	0.0050 (4)	0.0098 (4)	0.0049 (4)
N3	0.0253 (5)	0.0231 (5)	0.0179 (5)	0.0015 (4)	0.0063 (4)	0.0020 (4)
C1	0.0310 (7)	0.0213 (6)	0.0212 (6)	0.0025 (5)	0.0100 (5)	0.0049 (4)
C2	0.0236 (6)	0.0251 (6)	0.0200 (6)	0.0078 (5)	0.0038 (5)	0.0027 (4)
C3	0.0300 (7)	0.0332 (7)	0.0227 (6)	0.0077 (6)	−0.0012 (5)	−0.0023 (5)
C4	0.0270 (7)	0.0369 (7)	0.0388 (8)	−0.0018 (6)	−0.0029 (6)	−0.0080 (6)
C5	0.0258 (7)	0.0353 (7)	0.0435 (8)	−0.0040 (6)	0.0088 (6)	0.0002 (6)
C6	0.0240 (6)	0.0307 (6)	0.0310 (7)	0.0018 (5)	0.0115 (5)	0.0023 (5)
C7	0.0189 (6)	0.0212 (5)	0.0209 (6)	0.0057 (4)	0.0043 (4)	0.0007 (4)
C8	0.0288 (7)	0.0197 (6)	0.0185 (6)	0.0030 (5)	0.0092 (5)	−0.0010 (4)
C9	0.0259 (6)	0.0182 (5)	0.0146 (5)	−0.0004 (4)	0.0069 (4)	−0.0026 (4)
C10	0.0272 (6)	0.0175 (5)	0.0149 (5)	−0.0032 (4)	0.0082 (4)	−0.0014 (4)
C11	0.0274 (6)	0.0226 (6)	0.0203 (6)	−0.0002 (5)	0.0082 (5)	0.0004 (4)
C12	0.0260 (7)	0.0323 (7)	0.0289 (7)	−0.0009 (5)	0.0110 (5)	0.0000 (5)
C13	0.0282 (7)	0.0340 (7)	0.0297 (7)	−0.0046 (5)	0.0144 (5)	0.0010 (5)
C14	0.0251 (6)	0.0283 (6)	0.0252 (6)	−0.0067 (5)	0.0082 (5)	0.0061 (5)
C15	0.0648 (12)	0.0454 (9)	0.0409 (9)	−0.0056 (9)	0.0340 (9)	0.0029 (7)
C16	0.0288 (7)	0.0292 (7)	0.0306 (7)	−0.0061 (5)	0.0039 (6)	0.0094 (5)

Geometric parameters (Å, º) top

O1—C10	1.3782 (13)	C6—H6	0.980 (15)
O1—C13	1.3650 (16)	C8—C9	1.5142 (16)
O2—N3	1.3976 (12)	C8—H81	0.973 (14)
O2—C14	1.4547 (14)	C8—H82	0.984 (15)
N1—C1	1.3661 (15)	C9—C10	1.4511 (17)
N1—C7	1.3823 (15)	C10—C11	1.3621 (17)
N1—C8	1.4625 (15)	C11—C12	1.4247 (18)
N2—C1	1.3096 (16)	C11—H11	0.981 (15)
N2—C2	1.3917 (17)	C12—H12	0.948 (17)
N3—C9	1.2929 (15)	C13—C12	1.3440 (19)
C1—H1	0.981 (15)	C13—H13	0.964 (17)
C2—C3	1.3988 (18)	C14—C15	1.505 (2)
C2—C7	1.4043 (17)	C14—H14	0.988 (16)
C3—C4	1.381 (2)	C15—H151	1.02 (2)
C3—H3	0.974 (16)	C15—H152	0.98 (2)
C4—H4	0.966 (19)	C15—H153	0.98 (2)
C5—C4	1.402 (2)	C16—C14	1.5107 (19)
C5—H5	0.983 (17)	C16—H161	1.057 (18)
C6—C5	1.3836 (19)	C16—H163	0.982 (17)
C6—C7	1.3919 (18)	C16—H162	0.973 (19)

C13—O1—C10	106.74 (9)	N3—C9—C10	126.47 (10)
N3—O2—C14	110.34 (9)	N3—C9—C8	114.73 (11)
C1—N1—C7	106.29 (10)	C10—C9—C8	118.73 (10)
C1—N1—C8	127.66 (10)	C11—C10—O1	109.24 (10)
C7—N1—C8	126.05 (10)	C11—C10—C9	136.17 (11)
C1—N2—C2	104.24 (10)	O1—C10—C9	114.58 (10)
C9—N3—O2	111.22 (9)	C10—C11—C12	106.75 (11)
N2—C1—N1	114.13 (11)	C10—C11—H11	124.1 (9)
N2—C1—H1	125.1 (8)	C12—C11—H11	129.2 (9)
N1—C1—H1	120.7 (8)	C13—C12—C11	106.61 (12)
N2—C2—C3	129.89 (12)	C13—C12—H12	125.5 (10)
N2—C2—C7	110.19 (10)	C11—C12—H12	127.8 (10)
C3—C2—C7	119.91 (12)	C12—C13—O1	110.65 (11)
C4—C3—C2	117.53 (13)	C12—C13—H13	134.2 (10)
C4—C3—H3	123.9 (10)	O1—C13—H13	115.1 (9)
C2—C3—H3	118.6 (10)	O2—C14—C15	109.71 (11)
C3—C4—C5	121.71 (13)	O2—C14—C16	104.87 (10)
C3—C4—H4	118.9 (10)	C15—C14—C16	113.33 (12)
C5—C4—H4	119.4 (10)	O2—C14—H14	107.9 (9)
C6—C5—C4	121.81 (14)	C15—C14—H14	110.6 (9)
C6—C5—H5	118.2 (10)	C16—C14—H14	110.2 (9)
C4—C5—H5	120.0 (10)	C14—C15—H151	111.3 (11)
C5—C6—C7	116.20 (12)	C14—C15—H152	110.8 (12)
C5—C6—H6	121.9 (9)	H151—C15—H152	109.8 (17)
C7—C6—H6	121.9 (9)	C14—C15—H153	111.1 (11)
N1—C7—C6	132.02 (11)	H151—C15—H153	108.3 (15)
N1—C7—C2	105.14 (10)	H152—C15—H153	105.3 (16)
C6—C7—C2	122.83 (11)	C14—C16—H161	112.4 (9)
N1—C8—C9	111.54 (9)	C14—C16—H163	108.7 (10)
N1—C8—H82	108.4 (8)	H161—C16—H163	108.5 (14)
C9—C8—H82	108.8 (8)	C14—C16—H162	108.6 (11)
N1—C8—H81	107.7 (8)	H161—C16—H162	112.2 (14)
C9—C8—H81	111.0 (8)	H163—C16—H162	106.1 (14)
H82—C8—H81	109.4 (12)

C13—O1—C10—C11	0.18 (12)	C7—C2—C3—C4	0.80 (18)
C13—O1—C10—C9	−179.51 (10)	N2—C2—C7—N1	−0.13 (13)
C10—O1—C13—C12	−0.41 (14)	C3—C2—C7—N1	−179.70 (10)
C14—O2—N3—C9	−177.47 (9)	N2—C2—C7—C6	178.84 (11)
N3—O2—C14—C15	−82.98 (13)	C3—C2—C7—C6	−0.73 (18)
N3—O2—C14—C16	155.00 (9)	C2—C3—C4—C5	−0.2 (2)
C7—N1—C1—N2	0.10 (14)	C6—C5—C4—C3	−0.6 (2)
C8—N1—C1—N2	179.73 (11)	C7—C6—C5—C4	0.7 (2)
C1—N1—C7—C6	−178.81 (12)	C5—C6—C7—N1	178.63 (12)
C8—N1—C7—C6	1.55 (19)	C5—C6—C7—C2	−0.03 (18)
C1—N1—C7—C2	0.03 (12)	N1—C8—C9—N3	−100.58 (12)
C8—N1—C7—C2	−179.62 (10)	N1—C8—C9—C10	76.58 (13)
C1—N1—C8—C9	−104.20 (13)	N3—C9—C10—C11	−5.0 (2)
C7—N1—C8—C9	75.38 (14)	C8—C9—C10—C11	178.23 (12)
C2—N2—C1—N1	−0.17 (14)	N3—C9—C10—O1	174.60 (10)
C1—N2—C2—C3	179.70 (12)	C8—C9—C10—O1	−2.19 (14)
C1—N2—C2—C7	0.18 (13)	O1—C10—C11—C12	0.10 (13)
O2—N3—C9—C10	−1.02 (15)	C9—C10—C11—C12	179.69 (12)
O2—N3—C9—C8	175.89 (9)	C10—C11—C12—C13	−0.34 (14)
N2—C2—C3—C4	−178.67 (12)	O1—C13—C12—C11	0.46 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2	0.98 (2)	2.32 (2)	2.772 (2)	107 (1)
C13—H13···N2ⁱ	0.96 (2)	2.37 (2)	3.286 (2)	159 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.

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)	8.4290 (2), 17.7606 (3), 10.6017 (2)
β (°)	111.882 (1)
V (Å³)	1472.77 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.966, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	20597, 3356, 2803
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.111, 1.12
No. of reflections	3356
No. of parameters	259
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.28

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	0.98 (2)	2.32 (2)	2.772 (2)	107 (1)
C13—H13···N2ⁱ	0.96 (2)	2.37 (2)	3.286 (2)	159 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

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